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
• Mol file: 862907-04-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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:

tert-butyl 3-(5-chloro-2-methoxyphenyl)-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate (862907-03-7) → tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate (862907-04-8) + 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:

6-(Trifluoromethyl)-1H-indol-2,3-dione (343-69-1) → tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate (862907-04-8)

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:

3-trifluoromethylaniline (98-16-8) → tert-butyl (+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-6-(trifluoromethyl)-2-oxoindoline-1-carboxylate (862907-04-8)

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

upstream raw materials:

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

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

3-trifluoromethylaniline

t-butyl<3-(trifluoromethyl)phenyl>-carbamate

Downstream raw materials:

(S)-(+)-3-(5-chloro-2-methoxyphenyl)-3-fluoro-1,3-dihydro-6-(trifluoromethyl)-2H-indol-2-one