Sodium hydride → 1-[(5-Chloro-pyridin-2-ylcarbamoyl)-methyl]-2-(1-isopropyl-piperidin-4-ylcarbamoyl)-1H-indole-5-carboxylic acid methyl ester

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Reaction Steps

To a solution of 3 g 2-(1-Isopropyl-piperidin-4-ylcarbamoyl)-1H-indole-5-carboxylic acid methyl ester in 80 ml absolute DMF 419 mg NaH (60% in mineral oil) were added under an argon atmosphere. After stirring for 30 min. 2.179 g 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide were added and the reaction mixture stirred for 2 h at RT. Then additional 105 mg NaH (60% in mineral oil) and 1.089 g 2-Bromo-N-(5-chloro-pyridin-2-yl)-acetamide were added and the mixture stirred for 1 h at RT. The solvent was removed in vacuo and the residue purified by chromatography on silica gel using CH2Cl2/MeOH/HOAC/H2O=9/1/0.1/0.1. The fractions containing the product were concentrated and lyophilized in a water/CH3CN mixture. Yield: 3.68 g.

Provenance & Evidence