methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Base Information

• Chemical Name: methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate
• CAS No.: 1261744-93-7
• Molecular Formula: C₁₅H₁₂N₂O₂
• Molecular Weight: 252.272
• Mol file: 1261744-93-7.mol

Synonyms:methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Chemical Property of methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

There total 4 articles about methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-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:

methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (1190312-37-8) + phenylboronic acid (98-80-6) → methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (1261744-93-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In methanol; toluene; at 80 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid (479553-01-0) → methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (1261744-93-7)

Guidance literature:

Multi-step reaction with 4 steps

1: methanol; hexane; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2: 3-chloro-benzenecarboperoxoic acid / 1,2-dimethoxyethane / 22.5 h / 20 °C / Inert atmosphere

3: chloroformic acid ethyl ester; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; toluene / 24 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; chloroformic acid ethyl ester; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; 4: Suzuki coupling;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

4-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide (1201748-37-9) → methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (1261744-93-7)

Guidance literature:

Multi-step reaction with 2 steps

1: chloroformic acid ethyl ester; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; toluene / 24 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; chloroformic acid ethyl ester; potassium carbonate; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; toluene; 2: Suzuki coupling;

DOI:10.1016/j.bmc.2011.04.014

upstream raw materials:

1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

4-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide

methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

phenylboronic acid

Downstream raw materials:

6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate