Sodium Carbonate → N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide

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Reaction Conditions

Reaction Steps

To a solution of bromide 34 (1.0 g, 2.02 mmol, 1 eq) and 3-(trifluoromethyl)phenyl boronic acid (575 mg, 3.03 mmol, 1.5 eq, Aldrich, Milwaukee, Wis., USA) in dimethoxyethane (70 mL), was added sodium carbonate solution (9 mL of a 2 M solution) and tetrakis-triphenylphosphine palladium (233 mg, 0.1 eq). The mixture was stirred at 90° C. for 16 h, cooled to room temperature, and concentrated in vacuo. The resultant residue was partitioned between EtOAc and saturated sodium bicarbonate solution, dried (Na2SO4), concentrated in vacuo and purified by silica gel chromatography (0-40% EtOAc/hexane) to give 790 mg (72%) of N-(4-(4-methoxybenzyloxy)-3-(3-trifluoromethylphenyl)benzyl)-4-fluoro-N-methylbenzenesulfonamide (35). 1HNMR (CD3OD, 400 MHz): δ 7.84 (m, 3H), 7.65 (d, 1H), 7.44-7.54 (m, 3H), 7.18-7.30 (m, 5H), 7.04 (d, 1H), 6.85 (d, 2H), 5.02 (s, 2H), 4.14 (s, 2H), 3.80 (s, 3H), 2.63 (s, 3H). MS (ESI): MH+=560.1. HPLC (Method B) tR=4.57 min.

Provenance & Evidence