Pyridine → HCID 67287963, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-(6-chloro-4-(ethoxycarbonyl)chroman-7-yloxy)benzoic acid (Preparation B; 56 mg, 0.1486 mmol) in 1,2-dichloroethane (0.15 ml) and DMF (1 drop) was added oxalyl chloride (15.56 μl, 0.1783 mmol), and the reaction was stirred for 2 hours. To this, pyridine (0.6 ml) and 6-p-tolylpyridin-2-amine hydrochloride (36.08 mg, 0.1635 mmol) were added, and the reaction was heated to 80° C. for 16 hours. The reaction was diluted with EtOAc and washed with 10% citric acid, saturated sodium bicarbonate, and saturated sodium chloride. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated. The crude material was purified by silica gel chromatography, eluting with a gradient of 5-70% EtOAc/hexanes to yield the desired compound (49 mg, 0.09024 mmol, 60.72% yield).

Provenance & Evidence