4-Toluenesulfonyl chloride → HCID 22663271, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of N-(3,5-dichloro-pyridin-4-yl)-3-formyl-1H-indole-6-carboxamide (0.518 g, Example 18) in dimethylformamide at 0° C. was treated with sodium hydride (0.136 g). The mixture was stirred for 15 minutes, then cooled to −40° C. and then treated with 4-toluenesulphonyl chloride (0.325 g). The reaction mixture was gradually allowed to warm to −20° C. over a period of 90 minutes, then quenched with water (20 ml), then extracted three times with ethyl acetate (25 ml). The combined extracts were dried over sodium sulphate then evaporated to give the title compound (800 mg), which was used without further purification as a white solid, m.p. 245° C. [Elemental analysis:— C, 53.91; H, 3.34; N, 8.30%. Calculated for C22H15Cl2N3O4S:— C, 54.11; H, 3.10; N, 8.60%].

Provenance & Evidence