Potassium Carbonate → HCID 24955764, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid benzyl amide (2.0 g, 6.43 mmol) in toluene (30 mL), water (10 mL) and ethanol (10 mL) was added 1H-pyrazole-5-boronic acid (1.44 g, 12.9 mmol), Pd(PPh3)4 (0.74 g, 0.643 mmol), and potassium carbonate (2.67 g, 19.3 mmol). The resulting mixture was degassed three times and heated to 100° C. for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL), and washed with brine (2×100 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (ethyl acetate:hexane, 1:1) to provide 4-methyl-2-(2H-Pyrazol-3-yl)-thiazole-5-carboxylic acid benzylamide (1.25 g, 66% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 8.76 (t, J=4.0 Hz, 1H), 7.89 (d, J=4.0 Hz, 1H), 7.31-7.36 (m, 4H), 7.24-7.27 (m, 1H), 6.78 (d, J=4.0 Hz, 1H), 4.44 (d, J=4.0 Hz, 2H), 2.60 (s, 3H); MS (M+H)+=299.1; Rt=1.06 min; HRMS (M+H)+=299.10.

Provenance & Evidence