Pyridine → HCID 86651943, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbonitrile (246 mg, 1 mmol) in HOAc/pyridine (3 mL/6 mL) was added a solution of sodium hypophosphite (352 mg, 4 mmol) in H2O (3 mL), followed by Raney-Nickel 2400 (slurry in H2O, 0.2 mL). The resulting mixture was heated at 55° C. (oil temp.) for 1 h then cooled to rt. Water (30 mL) was added and the mixture was extracted with EtOAc (30 mL×3). The combined extracts were washed with H2O (20 mL×3), brine (10 mL) and dried (Na2SO4). Removal of solvent gave a yellow solution containing pyridine. H2O (60 mL) was added with swirling and large amounts of yellow precipitate formed which was collected by suction filtration and rinsed with H2O. After dying under high vacuum, the title compound (75 mg, 30%) was obtained as a beige solid. 1H NMR (400 MHz, DMSO-d6) δ 13.90 (s, 1H, NH), 10.14 (s, 1H, CHO), 8.57 (d, J=5.6 Hz, 2H), 8.40 (d, J=8.4 Hz, 1H), 8.20 (s, 1H), 7.89 (d, J=16.8 Hz, 1H), 7.73-7.69 (m, 3H), 7.55 (d, J=16.4 Hz, 1H). MS ESI 247.0 [M+H]+, calcd for [C15H11N3O+H]+ 247.1.

Provenance & Evidence