tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate

Base Information

• Chemical Name: tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate
• CAS No.: 1354547-63-9
• Molecular Formula: C₂₅H₂₈N₂O₄
• Molecular Weight: 420.508

Synonyms:tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate

Chemical Property of tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate

Chemical Property:

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Technology Process of tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate

There total 2 articles about tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-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: 49.0%

Methyl 4-(bromomethyl)benzoate (2417-72-3) + 1,3,4,9-Tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester (168824-94-0) → tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate (1354547-63-9)

Guidance literature:

1,3,4,9-Tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester; With potassium tert-butylate; In N,N-dimethyl-formamide; at 80 ℃; for 0.25h; Inert atmosphere;

Methyl 4-(bromomethyl)benzoate; In N,N-dimethyl-formamide; at 80 ℃; for 2h; Inert atmosphere;

DOI:10.1021/jm200773h

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate (1354547-63-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 16 h / 20 °C

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1.5 h / 20 °C / Inert atmosphere

2.2: 0.25 h / Inert atmosphere

With sodium hydride; triethylamine; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.8b01936

Reference yield: 76.0%

tert-butyl 9-(4-(methoxycarbonyl)benzyl)-1,3,4,9-tetrahydro-2H-pyrido[3,4-b]indole-2-carboxylate (1354547-63-9) → methyl 4-((3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)methyl)benzoate (783293-89-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 30 ℃; for 2h;

DOI:10.1021/jm200773h

upstream raw materials:

Methyl 4-(bromomethyl)benzoate

1,3,4,9-Tetrahydro-β-carboline-2-carboxylic acid tert-butyl ester

di-tert-butyl dicarbonate

Downstream raw materials:

4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzoic acid methyl ester

N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-β-carbolin-9-ylmethyl)benzamide trifluoroacetic acid salt

methyl 4-((3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)methyl)benzoate

methyl 4-((2-benzyl-3,4-dihydro-1H-pyrido[3,4-b]indol-9(2H)-yl)methyl)benzoate

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