937366-54-6

Basic information

• Product Name: PINACOL ESTER INDOLE-5-BORONIC ACID
• Synonyms: PINACOL ESTER INDOLE-5-BORONIC ACID;Indole-3-boronic acid pinacol ester;3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;3-Indoleboronic Acid Pinacol Ester
• CAS NO: 937366-54-6
• Molecular Formula: C₁₄H₁₈BNO₂
• Molecular Weight: 243.10922
• Mol File: 937366-54-6.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 396.0±15.0 °C(Predicted)
• Appearance: /
• Density: 1.11
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: 17.01±0.30(Predicted)
• CAS DataBase Reference: PINACOL ESTER INDOLE-5-BORONIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: PINACOL ESTER INDOLE-5-BORONIC ACID(937366-54-6)
• EPA Substance Registry System: PINACOL ESTER INDOLE-5-BORONIC ACID(937366-54-6)

Safety Data

• Hazardous Substances Data: 937366-54-6(Hazardous Substances Data)

Usage

Description

PINACOL ESTER INDOLE-5-BORONIC ACID is a versatile chemical compound that features an indole moiety and a boronic acid functional group. It is widely recognized for its utility in organic synthesis, where it serves as a building block for the creation of more complex molecular structures. The PINACOL ESTER group attached to the indole provides a convenient point for further chemical manipulation, while the boron atom within the boronic acid group facilitates cross-coupling reactions with a range of electrophiles. PINACOL ESTER INDOLE-5-BORONIC ACID is a staple in medicinal chemistry and pharmaceutical research, where it is employed in the design and synthesis of potential drug candidates. Moreover, PINACOL ESTER INDOLE-5-BORONIC ACID has demonstrated its potential as a valuable component in the development of innovative materials and chemical processes.

Uses

Used in Organic Synthesis:
PINACOL ESTER INDOLE-5-BORONIC ACID is used as a building block for the synthesis of complex organic molecules, leveraging its PINACOL ESTER group for further chemical manipulation and the boronic acid group for cross-coupling reactions with various electrophiles.
Used in Medicinal Chemistry and Pharmaceutical Research:
In the field of medicinal chemistry, PINACOL ESTER INDOLE-5-BORONIC ACID is utilized as a key component in the design and synthesis of potential drug candidates. Its unique structure allows for the development of new therapeutic agents with specific biological activities.
Used in the Development of New Materials and Chemical Processes:
PINACOL ESTER INDOLE-5-BORONIC ACID is employed as a versatile tool in the creation of innovative materials and the optimization of chemical processes, contributing to advancements in various scientific and industrial applications.

InChI:InChI=1S/C14H18BNO2/c1-13(2)14(3,4)18-15(17-13)11-9-16-12-8-6-5-7-10(11)12/h5-9,16H,1-4H3

Synthetic route

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 4h; Solvent; Temperature; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	78%

3-bromoindole (1484-27-1) + 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (61676-62-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Stage #1: 3-bromoindole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane In tetrahydrofuran; hexane at 20℃; for 5h;	70%

tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (942070-45-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
at 180℃; for 0.75h;	64%

indole (120-72-9) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Stage #1: indole; 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane With triethylamine In tetrahydrofuran at 80℃; for 0.333333h; Schlenk technique; Inert atmosphere; Stage #2: With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin at 80℃; for 4h; Schlenk technique; Inert atmosphere;	50%
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	7 %Chromat.

3‑(4,4,5,5‑tetramethyl‑1,3,2‑dioxaborolan‑2‑yl)‑1‑(triisopropylsilyl)‑1H‑indole (476004-82-7) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With tetrabutyl ammonium fluoride

1-(triisopropylsilyl)-1H-indole (123191-00-4) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / 1/2[IrCl(COD)]2-(4,4'-di-tert-butyl-2,2'-bipyridine) / octane / 16 h / 80 °C 2: TBAF View Scheme

bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 83 percent / 1/2[IrCl(COD)]2-(4,4'-di-tert-butyl-2,2'-bipyridine) / octane / 16 h / 80 °C 2: TBAF View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 2 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere; Glovebox 2: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox View Scheme

indole (120-72-9) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / benzene-d6 / 0.5 h / 80 °C / Inert atmosphere; Glovebox; Sealed tube 2: (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin / tetrahydrofuran / 4 h / 80 °C / Inert atmosphere; Glovebox 3: methanol / tetrahydrofuran / 20 °C / Inert atmosphere; Glovebox View Scheme
Multi-step reaction with 2 steps 1.1: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 5 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 0.33 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme
Multi-step reaction with 2 steps 1: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) / hexane / 2 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox 2: bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane / hexane / 4 h / 60 °C / Inert atmosphere; Schlenk technique; Glovebox View Scheme

1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With methanol In tetrahydrofuran at 20℃; Inert atmosphere; Glovebox;	139 mg
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0); 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane In hexane at 60℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	94 %Chromat.

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 0.166667h; Time; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 36 %Chromat. B 15 %Chromat. C 27 %Chromat.
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 0.333333h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 24 %Chromat. B 22 %Chromat. C 32 %Chromat.
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 1h; Time; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 6 %Chromat. B 25 %Chromat. C 51 %Chromat.

indole (120-72-9) + bis(pinacol)diborane (73183-34-3) → 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 2h; Time; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	A 12 %Chromat. B 72 %Chromat.

1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole + bis(pinacol)diborane (73183-34-3) → 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6)

Conditions	Yield
With bis(1,3-dimesityl-1H-imidazol-2(3H)-ylidene)nickel(0) In hexane at 60℃; for 4h; Inert atmosphere; Schlenk technique; Glovebox; regioselective reaction;	91 %Chromat.

4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 1,3-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole

Conditions	Yield
With triethylamine In tetrahydrofuran at 80℃; for 1h; Inert atmosphere; Sealed tube; Glovebox;	95%

3-bromo-(1-tert-butyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (862728-61-8) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 1-(tert-butyl)-3-(1H-indol-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 150℃; for 0.25h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Microwave irradiation;	70%

1,4-dibromo-2-nitrobenzene (3460-18-2) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(4-bromo-2-nitrophenyl)-1H-indole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In ethanol; water; toluene at 80℃; for 16h;	60%

2-nitrophenyl bromide (577-19-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(2-nitrophenyl)-1H-indole (56366-31-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium carbonate In ethanol; water; toluene at 80℃; for 16h;	60%

4-(4-chloro-6-methoxy-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole + trifluoroacetic acid (76-05-1) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → (x)C2HF3O2*C24H18FN5O2

Conditions	Yield
Stage #1: 4-(4-chloro-6-methoxy-9H-pyrimido[4,5-b]indol-7-yl)-3,5-dimethylisoxazole; 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,2-dimethoxyethane; water at 20℃; for 14h; Suzuki Coupling; Reflux; Stage #2: trifluoroacetic acid In 1,2-dimethoxyethane; water for 0.25h;	44%

3-bromo-4-methoxy-6-methyl-2H-pyran-2-one (670-35-9) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(1H-indol-3-yl)-4-methoxy-6-methyl-2H-pyran-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling;	42%

3-bromo-4-methoxy-6-methyl-2H-pyran-2-one (670-35-9) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(1H-indol-2-yl)-4-methoxy-6-methyl-2H-pyran-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling;	41%

3-bromo-4,6-dimethyl-2H-pyran-2-one (669-95-4) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(1H-indol-3-yl)-4,6-dimethyl-2H-pyran-2-one

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; for 24h; Suzuki Coupling;	38%

2,4,5-trichloropyrimidine (5750-76-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-(2,5-dichloropyrimidine-4-yl)-1H-indole (937366-57-9)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C22H22ClN5

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd(PPh3)4 / 1,2-dimethoxy-ethane 2: 2-methoxy-ethanol View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C25H27ClN6

Conditions	Yield
Multi-step reaction with 2 steps 1: Pd(PPh3)4 / 1,2-dimethoxy-ethane 2: 2-methoxy-ethanol View Scheme

N-[4-(2-bromothiazol-4-yl)-3-chlorophenyl]-1,1,1-trifluoro-methanesulfonamide + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → N-{3-chloro-4-[2-(1H-indol-3-yl)-1,3-thiazol-4-yl]phenyl}-1,1,1-trifluoromethanesulfonamide

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;	42 mg
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;	43 mg
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; N,N-dimethyl-formamide at 100℃; for 18h; Inert atmosphere;	42 mg

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 3-bromo-5,6-dihydroindolo[2,3-b]indole

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C26H17BrN2

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C View Scheme
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → indolo[2,3-b]indole

Conditions	Yield
Multi-step reaction with 2 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → 5,6-diphenyl-5,6-dihydroindolo[2,3-b]indole

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C26H16F2N2

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C26H15BrF2N2

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C44H31N3

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 3 h / 80 °C View Scheme
Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C 5: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 3 h / 80 °C View Scheme

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (937366-54-6) → C44H29F2N3

Conditions

Yield

Multi-step reaction with 5 steps 1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate; tetrabutylammomium bromide / toluene; ethanol; water / 16 h / 80 °C 2: triphenylphosphine / 1,2-dichloro-benzene / 16 h / 180 °C 3: copper(l) iodide; 1,10-Phenanthroline; potassium carbonate / N,N-dimethyl-formamide / 16 h / 150 °C 4: N-Bromosuccinimide / dichloromethane / 5 h / 0 - 20 °C 5: tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate / toluene / 3 h / 80 °C View Scheme

Upstream product

• 1484-27-1 3-bromoindole 
• 61676-62-8 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 73183-34-3 bis(pinacol)diborane 
• 120-72-9 indole 
• 25015-63-8 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane 
• 942070-45-3 tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate 
• 123191-00-4 1-(triisopropylsilyl)-1H-indole 
• 476004-82-7 3?(4,4,5,5?tetramethyl?1,3,2?dioxaborolan?2?yl)?1?(triisopropylsilyl)?1H?indole 

Downstream Products

• 937366-57-9 3-(2,5-dichloropyrimidine-4-yl)-1H-indole 
• 56366-31-5 3-(2-nitrophenyl)-1H-indole 

Relevant articles and documents

Ni-Catalyzed Traceless, Directed C3-Selective C-H Borylation of Indoles

A highly efficient and general protocol for traceless, directed C3-selective C-H borylation of indoles with [Ni(IMes)2] as the catalyst is reported. Activation and borylation of N-H bonds by [Ni(IMes)2] is essential to install a Bpin moiety at the N-position as a traceless directing group, which enables the C3-selective borylation of C-H bonds. The N-Bpin group which is formed is easily converted in situ back to an N-H group by the oxidative addition product of [Ni(IMes)2] and in situ-generated HBpin. The catalytic reactions are operationally simple, allowing borylation of a variety of substituted indoles with B2pin2 in excellent yields and with high selectivity. The C-H borylation can be followed by Suzuki-Miyaura cross-coupling of the C-borylated indoles in an overall two-step, one-pot process providing an efficient method for synthesizing C3-functionalized heteroarenes.

CONDENSED CYCLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

A condensed cyclic compound and an organic light-emitting device including the same, the condensed cyclic compound being represented by the following Formula 1:

Boc groups as protectors and directors for ir-catalyzed C-H borylation of heterocycles

(Chemical Equation Presented) Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions β to N. The Boc group can be removed on thermolysis