tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

Base Information

Chemical Name:tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate
CAS No.:862907-04-8
Molecular Formula:C₂₁H₁₈ClF₄NO₄
Molecular Weight:459.825
Hs Code.:

Synonyms:tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

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Chemical Property of tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

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Technology Process of tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

There total 8 articles about tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate 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:

: 862907-03-7
tert-butyl 3-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

: 862907-04-8
tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

: tert-butyl (-)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

Guidance literature:: With [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-); N-fluorobis(benzenesulfon)imide; In acetone; at 0 ℃; for 18h; Title compound not separated from byproducts;
DOI:10.1021/ja0513077

Reference yield:

: 343-69-1
6-(Trifluoromethyl)-1H-indol-2,3-dione

: 862907-04-8
tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: NaH / tetrahydrofuran / 1 h / 0 °C

1.2: 81 percent / tetrahydrofuran / 4 h / -20 - 20 °C

2.1: 76 percent / Et₃SiH; TFA / 48 h / 110 - 120 °C

3.1: 80 percent / EtMgBr / tetrahydrofuran / 3 h / 20 °C

4.1: N-fluorobenzenesulfonimide; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-) / acetone / 18 h / 0 °C

With triethylsilane; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-); ethylmagnesium bromide; sodium hydride; N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; In tetrahydrofuran; acetone;
DOI:10.1021/ja0513077

Reference yield:

: 98-16-8
3-trifluoromethylaniline

: 862907-04-8
tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1.1: 78 percent / 4 h / 80 °C

2.1: s-BuLi / cyclohexane; hexane; tetrahydrofuran / 3 h / -40 °C

2.2: 87 percent / cyclohexane; hexane; tetrahydrofuran / 1 h / -78 °C

3.1: 96 percent / aq. HCl / tetrahydrofuran / 6 h / Heating

4.1: NaH / tetrahydrofuran / 1 h / 0 °C

4.2: 81 percent / tetrahydrofuran / 4 h / -20 - 20 °C

5.1: 76 percent / Et₃SiH; TFA / 48 h / 110 - 120 °C

6.1: 80 percent / EtMgBr / tetrahydrofuran / 3 h / 20 °C

7.1: N-fluorobenzenesulfonimide; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-) / acetone / 18 h / 0 °C

With hydrogenchloride; triethylsilane; [Pd2((S)-DM-BINAP)2(μ-OH)2](2+)*2TfO(1-); ethylmagnesium bromide; sec.-butyllithium; sodium hydride; N-fluorobis(benzenesulfon)imide; trifluoroacetic acid; In tetrahydrofuran; hexane; cyclohexane; acetone;
DOI:10.1021/ja0513077