[2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester

Base Information

Chemical Name:[2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester
CAS No.:924627-41-8
Molecular Formula:C₂₃H₂₃N₃O₄
Molecular Weight:405.453
Hs Code.:

Synonyms:[2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester

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Chemical Property of [2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester

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Technology Process of [2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester

There total 4 articles about [2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester 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: 88.0%

: (4-cyano-2-iodo-phenyl)carbamic acid tert-butyl

: 156049-34-2
(E)-methyl 3-(2-isocyanophenyl)acrylate

: 924627-41-8
[2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester

Guidance literature:: (E)-methyl 3-(2-isocyanophenyl)acrylate; With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In acetonitrile; at 100 ℃;

(4-cyano-2-iodo-phenyl)carbamic acid tert-butyl; With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 50 ℃; Further stages.;
DOI:10.1055/s-2006-950328

Reference yield:

: 615-43-0
2-iodophenylamine

: 924627-41-8
[2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 100 percent / NaH / tetrahydrofuran / 24 h / 20 °C

2.1: 81 percent / Et₃N; P(o-tol)3 / Pd(OAc)2 / acetonitrile / 2.5 h / Heating

3.1: 85 percent / triphosgene; Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

4.1: Bu₃SnH; AIBN / acetonitrile / 100 °C

4.2: 88 percent / CuI / Pd(PPh₃)4 / dimethylformamide / 50 °C

With 2,2'-azobis(isobutyronitrile); bis(trichloromethyl) carbonate; tri-n-butyl-tin hydride; sodium hydride; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In tetrahydrofuran; dichloromethane; acetonitrile; 2.1: Heck coupling / 4.2: Stille coupling;
DOI:10.1055/s-2006-950328

Reference yield:

: 10113-39-0
N-formyl-2-iodoaniline

: 924627-41-8
[2-(2-tert-butoxycarbonylamino-5-cyanophenyl)-1H-indol-3-yl]acetic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: 81 percent / Et₃N; P(o-tol)3 / Pd(OAc)2 / acetonitrile / 2.5 h / Heating

2.1: 85 percent / triphosgene; Et₃N / CH₂Cl₂ / 1 h / 0 - 20 °C

3.1: Bu₃SnH; AIBN / acetonitrile / 100 °C

3.2: 88 percent / CuI / Pd(PPh₃)4 / dimethylformamide / 50 °C

With 2,2'-azobis(isobutyronitrile); bis(trichloromethyl) carbonate; tri-n-butyl-tin hydride; triethylamine; tris-(o-tolyl)phosphine; palladium diacetate; In dichloromethane; acetonitrile; 1.1: Heck coupling / 3.2: Stille coupling;
DOI:10.1055/s-2006-950328