Pyridine → HCID 67289903, compound

Participants

Reaction Steps

4-(6-Cyano-4-(methoxycarbonyl)chroman-7-yloxy)-3-methylbenzoic acid (0.103 g, 0.280 mmol) was dissolved in 4 mL dry DCM at ambient temperature under nitrogen. Oxalyl chloride (0.0489 mL, 0.561 mmol) was added to the reaction followed by 10 μL DMF. The solution was stirred at ambient temperature for 1 hour. The solution was concentrated and the residue was taken up in 4 mL dry DCE. 6-(Trifluoromethyl)pyridin-3-amine (0.136 g, 0.841 mmol), pyridine (0.0567 mL, 0.701 mmol) and DMAP (0.0034 g, 0.0280 mmol) were added and the solution was stirred at ambient temperature overnight. The reaction was poured into water, extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated. The crude material was purified by silica gel column chromatography, eluting with 30-50% ethyl acetate/hexanes, followed by a second silica gel chromatography eluting with 30% acetone/hexanes to provide the desired product (0.097 g, 68%).

Provenance & Evidence