Acetic Acid → HCID 86651943, compound

Participants

Reaction Conditions

Reaction Steps

The crude (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbonitrile was dissolved in DMF (10 mL). Pyridine (10 mL) and acetic acid (5 mL) were added, followed by NaH2PO2/H2O (1.76 g, 20 mmol/5 mL) and Raney-Nickel 2400 (slurry in H2O, 1 mL). The resulting mixture was heated at 60° C. for 1 h before cooling to rt. The mixture was diluted with H2O and extracted with EtOAc (50 mL×3). The combined extracts were dried (Na2SO4) and concentrated to give an orange liquid. H2O (50 mL) was added and the resulting suspension was sonicated, suction filtered, rinsed with H2O and dried to give crude (E)-3-(2-(pyridin-4-yl)vinyl)-1H-indazole-6-carbaldehyde (540 mg) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 13.90 (s, 1H), 10.15 (s, 1H), 8.57 (d, 2H, J=4.0 Hz), 8.40 (d, 1H, J=8.0 Hz), 8.20 (s, 1H), 7.89 (d, 1H, J=16.4 Hz), 7.73-7.68 (m, 3H), 7.55 (d, 1H, J=16.8 Hz); MS ESI 249.9 [M+H]+, calcd for [C23H16N4O+H]+ 250.1.

Provenance & Evidence