Water → 7-(3,5-Difluorobenzyloxy)-3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazole

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Reaction Steps

To the 3-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenyl)-4,5,6,7-tetrahydrobenzo[d]isoxazol-7-ol (48 mg, 0.15 mmol) in DMF (2 ml) at 0° C., was added NaH (7 mg, 0.18 mmol). The mixture was stirred for 10 min before addition of 1-(bromomethyl)-3,5-difluorobenzene. Stirring was continued for 1 hr before addition of water (3 mL) and extraction with ethyl acetate. The organic phase was washed with water, brine, dried over MgSO4 and concentrated. The crude product was purified by preparative TLC using 5% of MeOH in DCM as solvent to afford the title product. 1H NMR (CDCl3) δ: 7.82 (br. s., 1H), 7.53 (s, 1H), 7.30-7.40 (m, 214), 6.89-7.03 (m, 2H), 6.73 (t, J=9.0 Hz, 1H), 4.84 (d, J=12.9 Hz, 1H), 4.76 (d, J=13.7 Hz, 1H), 4.64 (t, J 3.7 Hz, 1H), 3.93 (s, 3H), 2.73-2.82 (m, 1H), 2.57-2.68 (m, 1H), 2.33 (br. s., 314), 2.17-2.26 (m, 1H), 1.87-2.07 (m, 3H). MS(M+H)+=452.

Provenance & Evidence