Potassium Carbonate → N-[4-(2,4-Dimethyl-thiazol-5-yl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (200 mg, 0.468 mmol, example 25, intermediate a), 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole (107.4 mg, 0.7 mmol, CAS RN 859833-13-9) and K2CO3 (193.75 mg, 1.4 mmol) in DMF (6 mL), taken in a sealed tube, was degassed well for 30 min with argon. To this mixture was added S-PHOS (50.1 mg, 0.25 mmol, CAS RN 657408-07-6) and Pd(PPh3)4 (54 mg, 0.05 mmol), and degassed again for 15 min. The reaction mixture was heated to 80° C. for 30 min irradiated with microwave. After the completion of reaction, it was cooled to room temperature, filtered through a bed of celite and the residue washed with EtOAc (50 mL). Volatilities were removed in vacuo and the resultant residue was diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, filtered, and evaporated. The crude residue was purified by column chromatography over silica gel (30-40% EtOAc in n-hexane) to afford the title compound as a pale yellow solid (15 mg, 7%). MS (ESI): m/z=460.1 [M+H]+.

Provenance & Evidence