5-Iodo-3-[(3,5-dibromo-4-hydroxyphenyl)methylene]-2-indolinone

Base Information

• Chemical Name: 5-Iodo-3-[(3,5-dibromo-4-hydroxyphenyl)methylene]-2-indolinone
• CAS No.: 220904-83-6
• Molecular Formula: C₁₅H₈Br₂INO₂
• Molecular Weight: 520.947
• Hs Code.: 2933790090
• UNII: B7W8RS1GG2
• DSSTox Substance ID: DTXSID10421368
• Nikkaji Number: J1.251.296A
• Wikidata: Q27077947
• Pharos Ligand ID: 4B55ZZ8KSJPH
• ChEMBL ID: CHEMBL72365
• Mol file: 220904-83-6.mol

Synonyms:5-iodo-3-((3,5-dibromo-4-hydroxyphenyl)methylene)-2-indolinone;GW 5074;GW-5074;GW5074

Chemical Property of 5-Iodo-3-[(3,5-dibromo-4-hydroxyphenyl)methylene]-2-indolinone

Chemical Property:

• Appearance/Colour: solid
• Vapor Pressure: 3.29E-13mmHg at 25°C
• Refractive Index: 1.789
• Boiling Point: 561.4 °C at 760 mmHg
• PKA: 5.86±0.25(Predicted)
• Flash Point: 293.3 °C
• PSA: 49.33000
• Density: 2.248 g/cm³
• LogP: 5.15250
• Storage Temp.: -20°C
• Solubility.: DMSO: soluble
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 520.79460
• Heavy Atom Count: 21
• Complexity: 447

Purity/Quality:

98%,99%, ^*data from raw suppliers

GW5074 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1I)C(=CC3=CC(=C(C(=C3)Br)O)Br)C(=O)N2
• Isomeric SMILES: C1=CC2=C(C=C1I)/C(=C/C3=CC(=C(C(=C3)Br)O)Br)/C(=O)N2
• Description: GW-5074 (220904-83-6) is a potent inhibitor of cRAF1 kinase (IC50 = 9 nM). Displays 100-fold selectivity for cRAF1 over CDK1, CDK2, c-src, ERK2, MEK, p38, Tie2, VEGFR2 and c-fm. GW-5074 displays neuroprotective effects in vivo via a mechanism that is independent of MEK, ERK, and Akt signaling. Cell permeable.
• Uses: GW5074 has been used as a specific inhibitor of cRaf1 in C2 murine skeletal myoblasts, HT-29 colorectal adenocarcinoma cell line and neutrophils.

Technology Process of 5-Iodo-3-[(3,5-dibromo-4-hydroxyphenyl)methylene]-2-indolinone

There total 2 articles about 5-Iodo-3-[(3,5-dibromo-4-hydroxyphenyl)methylene]-2-indolinone 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: 45.0%

3,5-dibromo-4-hydroxybenzaldehyde (2973-77-5) + 5-iodo-1,3-dihydro-indol-2-one (193354-13-1) → 3-(3,5-dibromo-4-hydroxy-benzylidene)-5-iodo-1,3-dihydro-indol-2-one (220904-83-6)

Guidance literature:

With piperidine; In ethanol; at 80 ℃; for 16h;

Reference yield:

2-oxoindole (59-48-3) → 3-(3,5-dibromo-4-hydroxy-benzylidene)-5-iodo-1,3-dihydro-indol-2-one (220904-83-6)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodo-succinimide; acetic acid / 16 h / 20 °C

2: piperidine / ethanol / 16 h / 80 °C

With piperidine; N-iodo-succinimide; acetic acid; In ethanol;

Reference yield: 2.3%

10-((1-((E)-(2-methyl-4-((E)-o-methylphenyldiazenyl)phenyl)diazenyl)naphthalene-2-yl)oxy)decyl methanesulfonate + 3-(3,5-dibromo-4-hydroxy-benzylidene)-5-iodo-1,3-dihydro-indol-2-one (220904-83-6) → 3-(3,5-dibromo-4-((10-((1-((E)-(2-methyl-4-((E)-o-methylphenyldiazenyl)phenyl)diazenyl)naphthalen-2-yl)oxy)decyl)oxy)benzylidene)-5-iodoindolin-2-one

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 80 ℃; for 16h;

upstream raw materials:

3,5-dibromo-4-hydroxybenzaldehyde

5-iodo-1,3-dihydro-indol-2-one

2-oxoindole

Refernces

• 1、 -. "Compounds for preventing or treating lipid metabolism-related diseases". Paragraph 0589; 0589-0591. . Retrieved 2021/10/27.