[1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester

Base Information

• Chemical Name: [1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester
• CAS No.: 346424-36-0
• Molecular Formula: C₂₂H₂₂ClNO₄
• Molecular Weight: 399.874
• Mol file: 346424-36-0.mol

Synonyms:[1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester

Chemical Property of [1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of [1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester

There total 4 articles about [1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl 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:

t-butyl 5-benzyloxy-1-(chlorobenzoyl)-2-methyl indole acetate → [1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester (346424-36-0)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In ethyl acetate; for 3h; under 2888.19 Torr;

DOI:10.1021/jm000483h

Reference yield:

levulinic acid t-butyl ester (2854-10-6) → [1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester (346424-36-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 62 percent / AcONa / acetic acid / 2 h / Heating

2.1: tBuOK / tetrahydrofuran / 0.33 h

2.2: 100 percent / tetrahydrofuran / 11 h

3.1: H₂; AcOH / Pd/C / ethyl acetate / 3 h / 2888.19 Torr

With potassium tert-butylate; hydrogen; sodium acetate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; acetic acid; ethyl acetate;

DOI:10.1021/jm000483h

Reference yield:

4-benzyloxyphenylhydrazine hydrochloride (52068-30-1,55974-70-4) → [1-(4-chloro-benzoyl)-5-hydroxy-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester (346424-36-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 62 percent / AcONa / acetic acid / 2 h / Heating

2.1: tBuOK / tetrahydrofuran / 0.33 h

2.2: 100 percent / tetrahydrofuran / 11 h

3.1: H₂; AcOH / Pd/C / ethyl acetate / 3 h / 2888.19 Torr

With potassium tert-butylate; hydrogen; sodium acetate; acetic acid; palladium on activated charcoal; In tetrahydrofuran; acetic acid; ethyl acetate;

DOI:10.1021/jm000483h

upstream raw materials:

levulinic acid t-butyl ester

4-benzyloxyphenylhydrazine hydrochloride

t-butyl 5-benzyloxy-2-methyl indole acetate

Downstream raw materials:

[5-(3-benzyloxy-propoxy)-1-(4-chloro-benzoyl)-2-methyl-1H-indol-3-yl]-acetic acid tert-butyl ester

5-methyl-4-oxo-hexanoic acid 3-tert-butoxycarbonylmethyl-1-(4-chloro-benzoyl)-2-methyl-1H-indol-5-yl ester

5-methyl-hexanoic acid 3-tert-butoxycarbonylmethyl-1-(4-chloro-benzoyl)-2-methyl-1H-indol-5-yl ester

O-Desmethyl-Indomethacin