1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester

Base Information

Chemical Name:1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester
CAS No.:99619-33-7
Molecular Formula:C₂₆H₃₅NO₅SSi
Molecular Weight:501.719
Hs Code.:

Synonyms:1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester

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Chemical Property of 1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester

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Technology Process of 1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester

There total 5 articles about 1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-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: 77.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 99619-32-6
1-<(4-methylphenyl)sulfonyl>-3-(2-hydroxyethyl)indole-2-acetic acid, methyl ester

: 99619-33-7
1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 40 ℃; for 12h;
DOI:10.1021/jo00352a001

Reference yield:

: 67593-10-6
1-tosyl-N,N-dimethyl-3-indoleglycolamide

: 99619-33-7
1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 63 percent / 2,4,6-trimethylbenzoic acid / 1.) 110 - 125 deg C, 10 min, 2.) 130 - 140 deg C, 10 min, 3.) 210 deg C, 3 h

2: 72 percent / P₄S₁₀ / tetrahydrofuran / 6 h / Irradiation; ultrasonic irradiation

3: 2.) 2 N HCl / 1.) CH₂Cl₂, 0 - 20 deg C, 30 min, 2.) water, THF, 23 h

4: 95 percent / NaBH₄ / methanol / 0.5 h

5: 77 percent / imidazole / dimethylformamide / 12 h / 40 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; tetraphosphorus decasulfide; mesitylenecarboxylic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00352a001

Reference yield:

: 67593-15-1
1-<(4-methylphenyl)sulfonyl>-3-<(N,N-dimethylcarbamyl)methyl>indole-2-acetic acid, methyl ester

: 99619-33-7
1-<(4-methylphenyl)sulfonyl>-3-<2-((tert-butyldimethylsilyl)oxy)ethyl>indole-2-acetic acid, methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 72 percent / P₄S₁₀ / tetrahydrofuran / 6 h / Irradiation; ultrasonic irradiation

2: 2.) 2 N HCl / 1.) CH₂Cl₂, 0 - 20 deg C, 30 min, 2.) water, THF, 23 h

3: 95 percent / NaBH₄ / methanol / 0.5 h

4: 77 percent / imidazole / dimethylformamide / 12 h / 40 °C

With 1H-imidazole; hydrogenchloride; sodium tetrahydroborate; tetraphosphorus decasulfide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1021/jo00352a001