HCID 68756556, compound → HCID 71818810, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (E)-methyl 4-(2-(6-cyano-1H-indazol-3-yl)vinyl)benzoate (606 mg, 2 mmol) in HOAc/pyridine/DMF (4 mL/8 mL/6 mL) was added a solution of NaH2PO2 (704 mg, 8 mmol) in H2O (4 mL), followed by Raney-Nickel 2400 (slurry in H2O, 0.4 mL). The resulting mixture was heated for 1 h at 55° C. (oil temp.). After cooling to rt, it was diluted with EtOAc (80 mL) and washed with H2O (30 mL). Aqueous layer was extracted with EtOAc (50 mL). Combined organic layers were washed with 2 N HCl (20 mL), H2O (20 mL) and dried (Na2SO4). Evaporation of solvent gave crude title compound as an orange solid which was triturated with EtOAc (10 mL), followed by suction filtration to give the title compound (240 mg, 39%) as light beige solid. The filtrate was concentrated, triturated with H2O, sonicated and the resulting precipitates were collected by suction filtration and rinsed with H2O, dried to give additional title compound (151 mg, 25%) as orange solid. 1H NMR (400 MHz, DMSO-d6) δ 13.82 (s, 1H), 10.14 (s, 1H), 8.40 (d, J=8.8 Hz, 1H), 8.18 (s, 1H), 7.97 (d, J=8.0 Hz, 2H), 7.88 (d, J=7.6 Hz, 2H), 7.77 (d, J=16.8 Hz, 1H), 7.79 (d, J=8.4 Hz, 1H), 7.64 (d, J=15.6 Hz, 1H), 3.86 (s, 3H); MS ESI 307.0 [M+H]+, calcd for [C18H14N2O3+H]+ 307.1.

Provenance & Evidence