Sodium borohydride → HCID 25174808, compound

Participants

Reaction Steps

To a solution of 3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[6-[2-(3-methoxy propyl)phenyl]-4-(trifluoromethyl)pyridin-3-yl]propanenitrile from step 5 (1 eq.) in EtOH (0.05M) at 0° C. was added nickel chloride (NiCl2; 1 eq.) and then portionwise sodium borohydride (3 eq.). The final mixture was stirred for 2 h at room temperature, poured in conc. ammonia and extracted with EtOAc. The organic extract was washed with water, brine, dried over Na2SO4, filtered and concentrated. Purification by column chromatography on silica gel, eluting with EtOAc/MeOH(NH3 2M) 10%, afforded the title compound as a colorless oil. 1H NMR (500 MHz, CD3OD): δ 8.91 (s, 1H), 7.63 (s, 1H), 7.44-7.32 (m, 4H), 7.19 (s, 2H), 7.02 (d, 2H), 6.80 (d, 2H), 4.34-4.27 (m, 4H), 3.56-3.49 (m, 1H), 3.27-3.15 (m, 6H), 3.11 (d, 2H), 3.06-2.99 (m, 1H), 2.80-2.70 (m, 2H), 2.29 (s, 3H), 1.71-1.64 (m, 2H).

Provenance & Evidence