Reaction #985327

ord-f07cb4c8e2b444a2ad2eedeaf712b641

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
CNC(=O)Cn1cc(C(=O)O)c2ccc(Cl)cc21
6-Chloro-1-methylcarbamoylmethyl-1H-indole-3-carboxylic acid

Reactants

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

Reagents

None

Solvents

ClCCCl
DCE

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 suspended 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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07351706B2uspto-grants-2008_04