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

HRID 898145Notes

Reaction equation

HRID 898145 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 acid

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 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.

Workup

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

Sources & evidence

ORD record
ord-f07cb4c8e2b444a2ad2eedeaf712b641
Source dataset
uspto-grants-2008_04
Patent number
US07351706B2

Reaction notes

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