Dimethylformamide → HCID 118071099, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 4G (5.0 g, 11.28 mmol) in DMF (50 mL) was added zinc cyanide (1.722 g, 14.66 mmol) and zinc (0.221 g, 3.38 mmol) to give a brown suspension. The reaction mixture was degassed under nitrogen for 15 min and added Pd2(dba)3 (0.516 g, 0.564 mmol) and dppf (0.625 g, 1.128 mmol). The reaction mixture was stirred at 90° C. for 18 h. The reaction mixture was quenched with water and the aqueous layer was extracted with ethyl acetate (3×50 mL) The combined organic layer was and washed with aqueous ammonia (2×50 mL), water, dried over Na2SO4, filtered and concentrated to afford crude product as brown semi-solid. The crude was purified by silica gel chromatography (40 g REDISEP® column, eluting with 50% EtOAc in hexane). Collected fractions concentrated together to afford Intermediate 4H (3 g, 78%) as white solid. MS(ES): m/z=343 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 7.73-7.78 (m, 1H), 7.62-7.68 (m, 1H), 7.43 (td, J=8.03, 5.52 Hz, 1H), 7.08-7.15 (m, 1H), 4.82 (s, 2H), 4.24 (t, J=5.52 Hz, 2H), 3.96 (t, J=5.27 Hz, 2H), 1.52 (s, 9H).

Provenance & Evidence