Water → HCID 18409465, compound

Participants

Reaction Steps

A mixture of 4-(4-fluorophenyl)-3-hydroxy-5-(4-(methylsulphonyl)phenyl)-pyrazole [(366 mg, 1.1 mmol), prepared according to the method of Example 5C, K2CO3 (152 mg, 1.1 mmol) in DMF (20 mL) at 50° C. was treated dropwise with a solution of 1-(bromomethyl)-4-fluorobenzene (0.141 mL, 1.1 mmol) in DMF (5 mL), and the mixture was stirred for 45 minutes. The reaction mixture was then poured into water and extracted with ethyl acetate. The acetate extract was washed with water, brine, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed (silica gel, 1:1 hexanes-ethyl acetate) to provide 3-(4-fluorobenzyloxy)-4-(4-fluorophenyl)-5-(4-(methyl-sulphonyl)phenyl)pyrazole (yield: 325 mg; 80%). MS (APCI+) m/z 441 (M+H)+; (APCI−) m/z 475 (M+Cl)−; 1H NMR (300 MHz, DMSO-d6) δ3.26 (s, 3H), 5.28 (s, 2H), 7.19 (m, 3H), 7.25 (m, 3H), 7.48 (m, 2H), 7.57 (d, J=9 Hz, 2H), 7.94 (d, J=9 Hz, 2H).

Provenance & Evidence