Hexane → 7-Chloro-3-methanesulfonyl-1H-indole

Participants

Reaction Steps

The crude N-(2-chloro-6-methanesulfonylmethyl-phenyl)-formimidic acid methyl ester of Step 5 was dissolved in dry DMSO (20 ml) and treated with 2 g powdered sodium hydroxide. The reaction mixture was vigorously stirred at room temperature for 1 h after which tlc (1:1 ethyl acetate:hexane, followed by 3:7) showed a single principal product, somewhat less polar than starting material. The reaction mixture was diluted with 100 ml of a 10% ammonium chloride solution and extracted with ethyl acetate, washed twice with water, and the crude solution was passed through a short silica gel column and eluted with ethyl acetate to remove colored impurities. The resulting crystalline 7-chloro-3-methanesulfonyl-1H-indole weighed 2.21 g.

Provenance & Evidence