Reaction #592255

ord-e290cce8ef914ea8a3ff203da847e888

Reaction equation

CNC(=O)Cn1cc(C(=O)C(F)(F)F)c2ccc(Cl)cc21
2-[6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N-methyl-acetamide
C[Si](C)(C)[O-].[Na+]
sodium trimethylsilanolate
CNC(=O)Cn1cc(C(=O)O)c2ccc(Cl)cc21
title compound
Yield 27.0%
CNC(=O)Cn1cc(C(=O)O)c2ccc(Cl)cc21
6-Chloro-1-methylcarbamoylmethyl-1H-indole-3-carboxylic acid
Yield 27.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Concentrationthe mixture was concentrated in vacuo
  2. 2
    Otherpurified by prep

Procedure

2-[6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N-methyl-acetamide was suspensed in DCE and treated with (2.2 eq.) of sodium trimethylsilanolate. After shaking at room temperature for 20 min, the mixture was concentrated in vacuo and purified by prep. HPLC to give the title compound in 27% yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07781436B2uspto-grants-2010_08