methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

Base Information

Chemical Name:methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate
CAS No.:936337-07-4
Molecular Formula:C₂₃H₂₁ClFNO₃
Molecular Weight:413.876
Hs Code.:

Synonyms:methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

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Chemical Property of methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

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Technology Process of methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

There total 15 articles about methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate 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:

: 571170-89-3
[5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester

: 97674-02-7
tributyl(1-ethoxyvinyl)stannane

: 936337-07-4
methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

Guidance literature:: [5-bromo-4-(4-chloro-benzyl)-7-fluoro-1,2,3,4-tetrahydro-cyclopenta[b]indol-3-yl]-acetic acid methyl ester; tributyl(1-ethoxyvinyl)stannane; With triphenyl-arsane; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In N,N-dimethyl-formamide; at 90 ℃; for 3.5h;

With hydrogenchloride; In N,N-dimethyl-formamide; at 50 ℃; for 2h;
DOI:10.1021/jm0603668

Reference yield:

: 393509-22-3
(+/-) 2-(7-fluoro-1,2,3-trihydrocyclopenta[2,3-b]indol-3-yl)acetic acid

: 936337-07-4
methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

Guidance literature:: Multi-step reaction with 8 steps

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

2.1: 117 g / AcOH; Zn / 1 h / 20 °C

3.1: HCl

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

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

5.1: 74.1 g / aq. NaOH / tetrahydrofuran; methanol / 0.25 h / 60 °C

6.1: 42 percent / (S)-(-)-1-(1-naphthyl)ethylamine salt / methanol

7.1: tetrahydrofuran; diethyl ether

8.1: Ph₃As / Pd₂(dba)3 / dimethylformamide / 3.5 h / 90 °C

8.2: 5.5 g / aq. HCl / dimethylformamide / 2 h / 50 °C

With pyridine; hydrogenchloride; sodium hydroxide; triphenyl-arsane; (S)-(-)-1-(1-naphthyl)ethylamine salt; sodium hydride; acetic acid; pyridinium hydrobromide perbromide; zinc; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; 8.1: Stille cross-coupling;
DOI:10.1021/jm0603668

Reference yield:

: 393509-23-4
(5-bromo-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

: 936337-07-4
methyl [(3R)-4-(4-chlorobenzyl)-7-fluoro-5-acetyl-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl]acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: HCl

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

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

3.1: 74.1 g / aq. NaOH / tetrahydrofuran; methanol / 0.25 h / 60 °C

4.1: 42 percent / (S)-(-)-1-(1-naphthyl)ethylamine salt / methanol

5.1: tetrahydrofuran; diethyl ether

6.1: Ph₃As / Pd₂(dba)3 / dimethylformamide / 3.5 h / 90 °C

6.2: 5.5 g / aq. HCl / dimethylformamide / 2 h / 50 °C

With hydrogenchloride; sodium hydroxide; triphenyl-arsane; (S)-(-)-1-(1-naphthyl)ethylamine salt; sodium hydride; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; methanol; diethyl ether; N,N-dimethyl-formamide; 6.1: Stille cross-coupling;
DOI:10.1021/jm0603668