Ethyl bromoacetate → (6-Chloro-3-methanesulfonyl-indol-1-yl)-acetic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

6-Chloro-3-methanesulfonyl-1H-indole (1.35 g, 5.88 mmole) was dissolved in anhydrous N-methylpyrrolidin-2-one (15 ml), cooled to 0° C. and placed under a nitrogen atmosphere. Sodium hydride (60% in oil, 0.28 g, 7 mmole) was added all at once and the mixture was stirred until the evolution of gas ceased (ca. 20-30 minutes). Ethyl bromoacetate (1.08 g, 6.47 mmole) was added all at once and the mixture was stirred for 30 minutes. The reaction mixture was partitioned between ethyl acetate and water, the organic layer was washed three times with water, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude material thus obtained was purified by chromatography on silica gel, eluting with ethyl acetate-hexane (1:9) to (4:6) to afford 1.463 g of (6-chloro-3-methanesulfonyl-indol-1-yl)-acetic acid ethyl ester.

Provenance & Evidence