Sodium trimethylsilanolate → 6-Chloro-1-methylcarbamoylmethyl-1H-indole-3-carboxylic acid

HRID 505073Notes

Reaction equation

HRID 505073 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16](=[O:21])C(F)(F)F)=[CH:7][N:8]2[CH2:11][C:12]([NH:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.C[Si](C)(C)[O-:24].[Na+]>ClCCCl>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]([OH:21])=[O:24])=[CH:7][N:8]2[CH2:11][C:12](=[O:13])[NH:14][CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23672319Sodium trimethylsilanolateHCID 667442882-[6-Chloro-3-(2,2,2-trifluoro-acetyl)-indol-1-yl]-N-methyl-acetamide

Product 1

HCID 597567026-Chloro-1-methylcarbamoylmethyl-1H-indole-3-carboxylic acidYield 27%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

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.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. custompurified by prep

Sources & evidence

ORD record
ord-e290cce8ef914ea8a3ff203da847e888
Source dataset
uspto-grants-2010_08
Patent number
US07781436B2

Reaction notes

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