Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-, methyl ester, (3R)-

Base Information

• Chemical Name: Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-, methyl ester, (3R)-
• CAS No.: 571170-89-3
• Molecular Formula: C21H18BrClFNO2
• Molecular Weight: 450.735
• Mol file: 571170-89-3.mol

Synonyms:

Chemical Property of Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-, methyl ester, (3R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-, methyl ester, (3R)-

There total 16 articles about Cyclopent[b]indole-3-acetic acid, 5-bromo-4-[(4-chlorophenyl)methyl]-7-fluoro-1,2,3,4-tetrahydro-, methyl ester, (3R)- 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: 100.0%

[(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid (393509-05-2) + diazomethane (186581-53-3,908094-01-9,334-88-3) → [5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester (571170-89-3)

Guidance literature:

In diethyl ether;

DOI:10.1002/jlcr.1146

Reference yield:

ethyl (2-oxocyclopentyl)acetate (20826-94-2) → [5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester (571170-89-3)

Guidance literature:

Multi-step reaction with 10 steps

1.1: p-TsOH*H₂O / toluene / 20 h / Heating

2.1: 252 g / nBu₄NCl / Pd(OAc)2 / dimethylformamide / 1 h / 80 °C

3.1: 92 percent / aq. NaOH / tetrahydrofuran; methanol / 0.25 h / 60 °C

4.1: pyridinium tribromide; pyridine / 0.75 h / -30 - 20 °C

5.1: 117 g / AcOH; Zn / 1 h / 20 °C

6.1: HCl

7.1: NaH / dimethylformamide / 0.33 h / 0 °C

7.2: dimethylformamide / 0.42 h / -50 - 0 °C

8.1: 74.1 g / aq. NaOH / tetrahydrofuran; methanol / 0.25 h / 60 °C

9.1: 42 percent / (S)-(-)-1-(1-naphthyl)ethylamine salt / methanol

10.1: tetrahydrofuran; diethyl ether

With pyridine; hydrogenchloride; sodium hydroxide; (S)-(-)-1-(1-naphthyl)ethylamine salt; tetrabutyl-ammonium chloride; sodium hydride; toluene-4-sulfonic acid; acetic acid; pyridinium hydrobromide perbromide; zinc; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm0603668

Reference yield:

[2-(2-bromo-4-fluoro-phenylimino)-cyclopentyl]-acetic acid ethyl ester (571170-84-8) → [5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester (571170-89-3)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 252 g / nBu₄NCl / Pd(OAc)2 / dimethylformamide / 1 h / 80 °C

2.1: 92 percent / aq. NaOH / tetrahydrofuran; methanol / 0.25 h / 60 °C

3.1: pyridinium tribromide; pyridine / 0.75 h / -30 - 20 °C

4.1: 117 g / AcOH; Zn / 1 h / 20 °C

5.1: HCl

6.1: NaH / dimethylformamide / 0.33 h / 0 °C

6.2: dimethylformamide / 0.42 h / -50 - 0 °C

7.1: 74.1 g / aq. NaOH / tetrahydrofuran; methanol / 0.25 h / 60 °C

8.1: 42 percent / (S)-(-)-1-(1-naphthyl)ethylamine salt / methanol

9.1: tetrahydrofuran; diethyl ether

With pyridine; hydrogenchloride; sodium hydroxide; (S)-(-)-1-(1-naphthyl)ethylamine salt; tetrabutyl-ammonium chloride; sodium hydride; acetic acid; pyridinium hydrobromide perbromide; zinc; palladium diacetate; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm0603668

upstream raw materials:

[(3R)-5-bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetic acid

diazomethane

(+/-) 2-(7-fluoro-1,2,3-trihydrocyclopenta[2,3-b]indol-3-yl)acetic acid

(5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

Downstream raw materials:

[4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester

[4-(4-chloro-benzyl)-7-fluoro-5-methanesulfonyl-1-oxo-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester

methanesulfonic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester

acetic acid 5-acetyl-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-ylmethyl ester