Dimethylacetamide → 5-(3-methyl-1-phenyl-1H-pyrazol-5-ylamino)-N-(thiazol-2-yl)pyridine-2-sulfonamide

Participants

Reaction Conditions

Reaction Steps

Into a Vial was added the 5-Bromo-pyridine-2-sulfonic acid thiazol-2-ylamide (75 mg, 0.00023 mol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (16 mg, 0.000028 mol), Tris(dibenzylideneacetone)dipalladium(0) (8.6 mg, 0.0000094 mol), 5-AMINO-3-METHYL-1-PHENYLPYRAZOLE (49 mg, 0.00028 mol) and N,N-Dimethylacetamide (3.0 mL, 0.032 mol). The mixture was sparged with argon for ˜5 min. Sodium tert-butoxide (68 mg, 0.00070 mol) was added and the reaction mixture was heated at 120° C. for 30 min in microwave. The reaction mixture was filtered through celite. The filtrate was diluted with Ethyl acetate and washed with 0.1 N HCl solution, water (3×) and brine, dried over sodium sulfate, filtered and was concentrated to give the crude product that was purified on ISCO (0% to 100% Ethyl acetate in CHCl3). 58 mg of the product was obtained as a light brown solid.

Provenance & Evidence