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

HRID 1097830Notes

Reaction equation

HRID 1097830 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-2a9301d5f3ce4303a72a68cdcb526ac4
Source dataset
uspto-grants-2012_03
Patent number
US08143281B2

Reaction notes

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