Hexachloroethane → 2-Chloro-N-(5-chloro-3-methoxy-2-pyrazinyl)-3-fluorobenzenesulphonamide

Participants

Reaction Conditions

Reaction Steps

A solution of N-(5-chloro-3-methoxy-2-pyrazinyl)-3-fluorobenzenesulphonamide (Example 130a) (0.159 g) in dry tetrahydrofuran (3 mL) was added to a stirred solution of lithium di-iso-propylamide (prepared from di-iso-propylamine (0.151 g) and n-butyl lithium (2.5M in hexanes)) in tetrahydrofuran (7.0 mL) at −78° C. The resulting solution was stirred at −78° C. for 15 minutes and then hexachloroethane (0.472 g) in tetrahydrofuran (2 mL) was added and the mixture allowed to attain room temperature over a 5 hour period. The reaction was quenched by the addition of 1N hydrochloric acid (10 mL) and extracted into ethyl acetate (2×20 mL). The combined extracts were dried (MgSO4), filtered and concentrated to afford an oil that was purified by chromatography on silica gel eluting with ethyl acetate/iso-hexane mixtures gave the titled compound (0.086 g) as a white solid.

Provenance & Evidence