Sodium hydride → 2-Phenoxymethyl-1-(4-trifluoromethylsulfanyl-benzyl)-1H-indole-5-carboxylic acid methyl ester

HRID 507229

Reaction equation

HRID 507229 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][C:9]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:8]2)=[O:4].[H-].[Na+].Br[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]([F:36])([F:35])[F:34])=[CH:28][CH:27]=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]([F:36])([F:34])[F:35])=[CH:28][CH:27]=1)[C:9]([CH2:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:8]2)=[O:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27778824-(Trifluoromethylthio)benzyl bromideHCID 597322132-Phenoxymethyl-1H-indole-5-carboxylic acid methyl ester

Product 1

HCID 684637372-Phenoxymethyl-1-(4-trifluoromethylsulfanyl-benzyl)-1H-indole-5-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

30 mg of 2-phenoxymethyl-1H-indole-5-carboxylic acid methyl ester were dissolved in 1 ml of THF and treated with 5 mg NaH (60%) at 0° C. for 15 min. 1.2 eq. of 1-bromomethyl-4-trifluoromethylsulfanyl-benzene were added and the reaction stirred for 1.5 h. The solvent was evaporated and the product extracted from methylenchloride/water. The product was purified by preparative HPLC. MS(ISP): 472.5 (M+H)+.

Workup

  1. customThe solvent was evaporated
  2. extractionthe product extracted from methylenchloride/water
  3. customThe product was purified by preparative HPLC

Sources & evidence

ORD record
ord-7ad017e3cbfa4f3da88f8e255b9ba8ce
Source dataset
uspto-grants-2010_08
Patent number
US07786128B2

Linked notes

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