methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Base Information

• Chemical Name: methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• CAS No.: 1422376-79-1
• Molecular Formula: C₂₀H₁₈N₂O₃
• Molecular Weight: 334.375
• Mol file: 1422376-79-1.mol

Synonyms:methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Chemical Property of methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate

There total 2 articles about methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-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: 75.0%

benzoyl chloride (98-88-4) + methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate (79815-18-2) → methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (1422376-79-1)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 9h; Reflux;

DOI:10.1021/jm301788a

Reference yield:

(S)-tryptophan methyl ester hydrochloride (7524-52-9,26988-71-6,5619-09-0,14907-27-8,41222-70-2,67557-19-1,109492-62-8) → methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (1422376-79-1)

Guidance literature:

Multi-step reaction with 2 steps

1: water; methanol / 5 h / 20 °C

2: triethylamine / tetrahydrofuran / 9 h / Reflux

With triethylamine; In tetrahydrofuran; methanol; water; 1: |Pictet-Spengler Synthesis;

DOI:10.1021/jm301788a

Reference yield: 73.0%

methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (1422376-79-1) + methyl iodide (74-88-4) → 2-benzoyl-9-methyl-1,2,3,4-tetrahydropyrido[3,4-b]indole-3-carboxylic acid (1422376-87-1)

Guidance literature:

methyl 2-benzoyl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 5 ℃; for 0.25h;

methyl iodide; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; for 9h;

With acetic acid; In water; pH=6;

DOI:10.1021/jm301788a

upstream raw materials:

(S)-tryptophan methyl ester hydrochloride

benzoyl chloride

methyl (3S)-1,2,3,4-tetrahydro-β-carboline-3-carboxylate

Downstream raw materials:

dimethyl 3-phenyl-6-methyl-6,11-dihydro-5H-indolizino-[6,7-b]indole-1,2-dicarboxylate

(3-(phenyl)-6-methyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl)dimethanol

[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(ethylcarbamate)

[6-methyl-3-phenyl-6,11-dihydro-5H-indolizino [6,7-b]indole-1,2-diyl]bis(methylene)bis(iso propylcarbamate)