Nitrogen → HCID 118061472, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Intermediate 314D (500 mg, 1.639 mmol) in DMF (10 mL) was added Zn(CN)2 (289 mg, 2.458 mmol) and the reaction mixture was degassed with N2 gas for 15 min Pd2(dba)3 (75 mg, 0.082 mmol) and dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (67.3 mg, 0.164 mmol) were then added and the reaction mixture was heated at 120° C. for 1 h. The reaction mixture was cooled to RT, diluted with water (50 mL) and extracted with EtOAc (3×40 mL) The combined organic layer was washed with water, brine, dried over Na2SO4, filtered and the filtrate concentrated. The crude product was purified by silica gel chromatography (24 g REDISEP® column, eluting with 10% EtOAc in hexane). Fractions containing the product were combined and evaporated to afford Intermediate 314E as a colorless liquid (350 mg, 85%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.87 (d, J=8.5 Hz, 2H), 7.58 (d, J=8.5 Hz, 2H), 3.62 (s, 3H), 3.51-3.37 (m, 2H), 3.28-3.13 (m, 2H).

Provenance & Evidence