Water → HCID 15430590, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1.146 g (3.1 mmol) of the product from Example 3 in 31 mL of DMF was added 0.137 g (3.42 mmol) of 60% sodium hydride. The resulting mixture was stirred for 30 min at 25° C. and then 0.42 mL (3.50 mmol) of benzyl bromide was added all at once. This reaction mixture was stirred for 10 hr at 55° C. and then poured into water and extracted with ether. The combined organics were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to provide a white solid which was recrystallized from ethyl acetate/Hexanes to provide 1.364 g (95%) of the desired product. 1H NMR(CDCl3): 7.7 ppm (dd, 2H, Ar), 7.1-7.4 (m, 5H, Ar), 6.9 ppm (dd, 2H, Ar), 4.5-4.7 ppm (AB quartet, 2H, CH2—Ar), 3.9 ppm (s, 3H, OMe), 4.0 ppm (m, 1H, N—CH), 2.9 ppm (m, 1H, CH—CO2—), 1.0-2.3 ppm (m, 17H, hydrocarbon protons).

Provenance & Evidence