Tert-butyl 6-formyl-1H-indole-1-carboxylate

Base Information

• Chemical Name: Tert-butyl 6-formyl-1H-indole-1-carboxylate
• CAS No.: 127956-28-9
• Molecular Formula: C14H15NO3
• Molecular Weight: 245.278
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID401228891
• Mol file: 127956-28-9.mol

Synonyms:TERT-BUTYL 6-FORMYL-1H-INDOLE-1-CARBOXYLATE;127956-28-9;tert-butyl 6-formylindole-1-carboxylate;MFCD11877853;1-Boc-6-formyl-1H-indole;1-(tert-butoxycarbonyl)-1H-indole-6-carboxaldehyde;SCHEMBL1056142;1-Boc-1H-indole-6-carbaldehyde;ZJOBUJIAVBTRMD-UHFFFAOYSA-N;DTXSID401228891;AKOS015959845;MB10431;LS-05250;SY067834;CS-0055865;D94896;1,1-Dimethylethyl 6-formyl-1H-indole-1-carboxylate;6-formyl-indole-1-carboxylic acid tert-butyl ester;TERT-BUTYL6-FORMYL-1H-INDOLE-1-CARBOXYLATE;6-formyl-1H-indole-1-carboxylic acid, 1,1-dimethylethyl ester

Chemical Property of Tert-butyl 6-formyl-1H-indole-1-carboxylate

Chemical Property:

• Boiling Point: 380.0±34.0 °C(Predicted)
• PSA: 48.30000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.23700
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 245.10519334
• Heavy Atom Count: 18
• Complexity: 334

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl 6-formyl-1H-indole-1-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC2=C1C=C(C=C2)C=O

Technology Process of Tert-butyl 6-formyl-1H-indole-1-carboxylate

There total 6 articles about Tert-butyl 6-formyl-1H-indole-1-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

indole-6-carboxaldehyde (1196-70-9) + di-tert-butyl dicarbonate (24424-99-5) → 1-(tert-butoxycarbonyl)-1H-indole-6-carboxaldehyde (127956-28-9)

Guidance literature:

With potassium tert-butylate; at 0 - 20 ℃; for 72h;

DOI:10.1021/jo025964i

Reference yield: 50.0%

(1-(tert-butoxycarbonyl)-1H-indol-6-yl)boronic acid + Glyoxilic acid (298-12-4) → 1-(tert-butoxycarbonyl)-1H-indole-6-carboxaldehyde (127956-28-9)

Guidance literature:

With 1,2,3,4-tetrahydroisoquinoline; In acetonitrile; at 20 ℃; Green chemistry;

DOI:10.1002/anie.201703127

Reference yield:

6-methylindole (3420-02-8) → 1-(tert-butoxycarbonyl)-1H-indole-6-carboxaldehyde (127956-28-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / 4-DMAP

2: 69 percent / NBS/dibenzoyl peroxide / CCl₄ / 0.42 h / 80 °C / Irradiation

3: 1.) DMSO/NaHCO₃, 2.) (BOC)2O/DMAP / 1.) DMSO, 150 deg C, 20 min; 2.) CH₃CN, 25 deg C, 10 min

With dmap; N-Bromosuccinimide; di-tert-butyl dicarbonate; sodium hydrogencarbonate; dimethyl sulfoxide; dibenzoyl peroxide; dmap; In tetrachloromethane;

DOI:10.1016/S0040-4039(01)93319-2

upstream raw materials:

6-(bromomethyl)-1-(tert-butoxycarbonyl)indole

indole-6-carboxaldehyde

di-tert-butyl dicarbonate

6-methylindole

Downstream raw materials:

2-(1H-indol-6-yl)acetonitrile

2-(indol-6-yl)acetic acid

3-[6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indol-1-yl]-propionic acid ethyl ester

6-(4',5'-difluoro-2'-methoxy-biphenyl-4-yloxymethyl)-indole-1-carboxylic acid tert-butyl ester

Refernces

• 1、 Elahi-Mohassel, Synah,Girgis, Michael,Paige, Mikell,Petruncio, Greg. "Copper-catalyzed sp3-sp3 cross-coupling of turbo grignards with benzyl halides". supporting information. . Retrieved 2021/11/17.
• 2、 Gerasyuto, Aleksey I.,Arnold, Michael A.,Wang, Jiashi,Chen, Guangming,Zhang, Xiaoyan,Smith, Sean,Woll, Matthew G.,Baird, John,Zhang, Nanjing,Almstead, Neil G.,Narasimhan, Jana,Peddi, Srinivasa,Dumble, Melissa,Sheedy, Josephine,Weetall, Marla,Branstrom, Arthur A.,Prasad,Karp, Gary M.. "Discovery and Optimization of Indolyl-Containing 4-Hydroxy-2-Pyridone Type II DNA Topoisomerase Inhibitors Active against Multidrug Resistant Gram-negative Bacteria". . p. 4456 - 4475. Retrieved 2018/05/15.