N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide

Base Information

• Chemical Name: N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide
• CAS No.: 1374875-31-6
• Molecular Formula: C₂₁H₂₀N₂O₂
• Molecular Weight: 332.402

Synonyms:N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide

Chemical Property of N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide

Chemical Property:

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Technology Process of N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide

There total 2 articles about N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide 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: 26.0%

p-methylanizole (104-93-8) + N,1-dimethyl-N-(prop-2-ynyl)-1H-indole-3-carboxamide (1374875-42-9) → N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide (1374875-31-6)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; at 60 ℃; for 6h; Inert atmosphere;

DOI:10.1002/adsc.201200092

Reference yield:

1-methyl-3-indolecarboxylic acid (32387-21-6) → N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide (1374875-31-6)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 40 °C

2.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; triethylamine / tetrahydrofuran / 6 h / 60 °C / Inert atmosphere

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

DOI:10.1002/adsc.201200092

Reference yield: 85.0%

N-(3-(4-methoxyphenyl)prop-2-ynyl)-N,1-dimethyl-1H-indole-3-carboxamide (1374875-31-6) → 5-(4-methoxyphenyl)-2,10-dimethyl-3,10-dihydro-2H-azepino[3,4-b]indol-1-one (1273578-28-1)

Guidance literature:

With C₂₈H₃₆AuF₆NO₆PS₂; In toluene; at 80 ℃; for 2h;

DOI:10.1002/adsc.201200092

upstream raw materials:

p-methylanizole

N,1-dimethyl-N-(prop-2-ynyl)-1H-indole-3-carboxamide

1-methyl-3-indolecarboxylic 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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