Cesium fluoride → N-[4-Methyl-5-(4-phenylsulfonylaminopyridin-2-yl)-1,3-thiazol-2-yl]acetamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(2-bromopyridin-4-yl)benzenesulfonamide (700 mg), 2-acetamido-4-methylthiazole (384 mg), palladium(II) acetate (41 mg), caesium fluoride (1.01 g), tri-tert-butylphosphine (0.34M solution in hexane, 1.06 mL) and DMSO (20 mL) was purged with nitrogen. The resultant mixture was heated to 150° C. for 5 hours under an atmosphere of nitrogen. The bulk of the DMSO was evaporated and the residue was treated with water (40 mL). Water was decanted from the resultant gum which was purified by column chromatography on silica using a solvent gradient of 2% to 5% methanol in dichloromethane as eluent. There was thus obtained the title compound as a solid (116 mg); 1H NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 2.44 (s, 3H), 6.93 (d, 1H), 7.32 (s, 1H), 7.60-7.70 (m, 3H), 7.91 (m, 2H), 8.29 (d, 1H), 11.25 (s, 1H), 12.13 (s, 1H); Mass Spectrum: M+H+ 389.

Provenance & Evidence