Methyl 6-bromo-3-formyl-1H-indole-4-carboxylate

Base Information

• Chemical Name: Methyl 6-bromo-3-formyl-1H-indole-4-carboxylate
• CAS No.: 1353636-63-1
• Molecular Weight: 282.09
• Mol file: 1353636-63-1.mol

Synonyms:Methyl 6-bromo-3-formyl-1H-indole-4-carboxylate

Chemical Property of Methyl 6-bromo-3-formyl-1H-indole-4-carboxylate

Chemical Property:

• Boiling Point: 451.0±40.0 °C(Predicted)
• PKA: 13.37±0.30(Predicted)
• Density: 1.682±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

Methyl6-Bromo-3-formyl-1H-indole-4-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 6-bromo-3-formyl-1H-indole-4-carboxylate

There total 1 articles about Methyl 6-bromo-3-formyl-1H-indole-4-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:

N,N-dimethyl-formamide (68-12-2,33513-42-7) + methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate (107650-22-6) → methyl 6-bromo-3-formyl-1H-indole-4-carboxylate (1353636-63-1)

Guidance literature:

N,N-dimethyl-formamide; With trichlorophosphate; at 0 ℃; for 0.5h;

methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate; at 0 - 20 ℃; for 2.5h;

DOI:10.1016/j.bmcl.2016.11.080

Reference yield:

methyl 6-bromo-3-formyl-1H-indole-4-carboxylate (1353636-63-1) → methyl 3-methyl-6-(4-(morpholinomethyl)phenyl)-1-(tetrahydro-2H-pyran-4-yl)indoline-4-carboxylate

Guidance literature:

Multi-step reaction with 4 steps

1.1: zinc(II) iodide; sodium cyanoborohydride / 1,2-dichloro-ethane / 16 h / 20 °C

2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C

3.1: acetic acid / dichloromethane / 0.5 h / 20 °C

3.2: 16 h / 20 °C

4.1: sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 15 h / 90 °C / Inert atmosphere

With triethylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium cyanoborohydride; sodium carbonate; acetic acid; trifluoroacetic acid; zinc(II) iodide; In 1,4-dioxane; dichloromethane; water; 1,2-dichloro-ethane; 4.1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.11.080

Reference yield:

methyl 6-bromo-3-formyl-1H-indole-4-carboxylate (1353636-63-1) → 1-(cyclopropylmethyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-methyl-6-(4-(morpholinomethyl)phenyl)indoline-4-carboxamide + 1-(cyclopropylmethyl)-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-3-methyl-6-(4-(morpholinomethyl)phenyl)indoline-4-carboxamide

Guidance literature:

Multi-step reaction with 5 steps

1.1: zinc(II) iodide; sodium cyanoborohydride / 1,2-dichloro-ethane / 16 h / 20 °C

2.1: triethylsilane; trifluoroacetic acid / dichloromethane / 16 h / 20 °C

3.1: acetic acid / dichloromethane / 0.5 h / 20 °C

3.2: 16 h / 20 °C

4.1: trimethylaluminum / toluene; tetrahydrofuran / 18 h

5.1: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine / dimethyl sulfoxide / 16 h / 20 °C

With triethylsilane; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; trimethylaluminum; sodium cyanoborohydride; acetic acid; triethylamine; trifluoroacetic acid; zinc(II) iodide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; toluene; 5.1: |Suzuki Coupling;

DOI:10.1016/j.bmcl.2016.11.080

upstream raw materials:

N,N-dimethyl-formamide

methyl 6-bromo-1-isopropyl-3-methyl-1H-indole-4-carboxylate

Refernces