Potassium Carbonate → HCID 59293415, compound

Participants

Reaction Conditions

Reaction Steps

1-(1-(2,2-Dimethoxyethyl)-1H-indazol-5-yl)-2-oxo-1,2-dihydropyridin-4-yl trifluoromethanesulfonate (2.66 mg, 5.95 mmol), phenylvinylboronic acid (2.23 g, 14.8 mmol), K2CO3 (2.05 g, 14.8 mmol) and PdCl2dppf (500 mg, 0.595 mmol) were stirred in DMSO (15 mL) under vacuum for 30 min. The flask was flushed with nitrogen and the mixture was heated at 80° C. for 1 h. Upon cooling, the mixture was diluted with methylene chloride, washed with 5% lithium chloride solution (5×), dried, concentrated, and the residue was purified by column chromatography (120 g ISCO column eluting with methylene chloride and a methanol/ammonia mixture (10:1); gradient 100% methylene chloride to 10% methanol/ammonia mixture (10:1) over 60 min at 40 mL/min) to provide the title compound (2.08 g, 87%): 1H NMR (500 MHz, CD3OD) 8.06 (s, 1H), 7.72 (d, J=17 Hz, 1H), 7.60-7.54 (m, 3H), 7.45-7.34 (m, 5H), 7.23 (d, J=16.6 Hz, 1H), 6.95 (d, J=16.6 Hz, 1H), 6.68 (d, J=1.5 Hz, 1H), 6.54-6.51 (dd, J=7.3, 1.8 Hz, 1H), 4.78 (t, J=5.3 Hz, 1H), 4.51 (t, J=5.3 Hz, 2H), 3.38 (s, 6H).

Provenance & Evidence