Methyl iodide → 3-(Cyanomethyl)-N,N-dimethyl-1H-indole-5-ethanesulphonamide

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Reaction Steps

Iodomethane (1.1 ml) was added to a stirred solution of the product of Stage (iii) (2.7 g) in dry dimethylsulphoxide (30 ml) and the resulting solution stirred at room temperature for 10 min. Potassium cyanide (2.7 g) was added, and the resulting mixture stirred at room temperature overnight. The mixture was partitioned between sodium carbonate, (2N, 300 ml) and ethyl acetate (2×100 ml). The combined extracts were dried (Na2SO4) and evaporated in vacuo to give an oil which was purified by `flash` chromatography (J, 5 cm col.) to give the title compound as a solid (1.3 g) m.p. 105°-107°.

Provenance & Evidence