1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide

Base Information

• Chemical Name: 1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide
• CAS No.: 1273578-14-5
• Molecular Formula: C₂₁H₂₀N₂O₂
• Molecular Weight: 332.402

Synonyms:1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide

Chemical Property of 1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide

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Technology Process of 1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide

There total 2 articles about 1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide 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: 31.0%

1-methyl-1H-indole-2-carboxylic acid methyl-prop-2-ynyl-amide (906543-07-5) + para-iodoanisole (696-62-8) → 1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide (1273578-14-5)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; for 20h; Inert atmosphere; Sealed tube; Heating;

DOI:10.1039/c0ob00728e

Reference yield:

N-methyl-1H-indole-2-carboxylic acid (16136-58-6) → 1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide (1273578-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; 1,1'-carbonyldiimidazole / tetrahydrofuran / 1.5 h / 20 °C / Inert atmosphere

1.2: 40 °C / Inert atmosphere

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 20 h / Inert atmosphere; Sealed tube; Heating

With dmap; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; 1,1'-carbonyldiimidazole; In tetrahydrofuran; 2.1: Sonogashira reaction;

DOI:10.1039/c0ob00728e

Reference yield: 78.0%

1-methyl-1H-indole-2-carboxylic acid [3-(4-methoxy-phenyl)-prop-2-ynyl]-methyl-amide (1273578-14-5) → 5-(4-methoxyphenyl)-2,10-dimethyl-3,10-dihydro-2H-azepino[3,4-b]indol-1-one (1273578-28-1)

Guidance literature:

With platinum(II) chloride; In dichloromethane; at 50 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1039/c0ob00728e

upstream raw materials:

1-methyl-1H-indole-2-carboxylic acid methyl-prop-2-ynyl-amide

para-iodoanisole

N-methyl-1H-indole-2-carboxylic acid

Downstream raw materials:

5-(4-methoxyphenyl)-2,10-dimethyl-3,10-dihydro-2H-azepino[3,4-b]indol-1-one

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