Dimethylformamide → [5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-3-(dimethylamino)furo[2,3-b]pyridin-2-yl](pyridin-3-yl)methanone

Participants

Reaction Conditions

Reaction Steps

A solution of 0.050 g (0.101 mmol) of the product from Example 26 in DMF (1 mL) at 0° C. was treated with sodium hydride (0.008 g; 60% dispersion; 0.213 mmol). After the addition, the reaction mixture was stirred for 20 minutes at 0° C., and then treated with iodomethane (19 μL; 0.303 mmol). The reaction was warmed to room temperature and stirred for 1 h. The reaction was quenched with saturated NaHCO3 solution. The reaction mixture was partitioned between ethyl acetate and saturated NaHCO3 solution. The organic layer was washed twice with saturated NaHCO3 solution, brine, dried (Na2SO4), filtered, and concentrated in vacuo. Purification by MPLC (silica gel; 0% to 50% ethyl acetate-hexane gradient) gave the title compound. HPLC/MS: 521.9 (M+1), 523.9 (M+3); Rt=3.96 min.

Provenance & Evidence