Phosphorus oxychloride → HCID 86703283, compound

Participants

Reaction Steps

To a solution of 6-(6-cyclopropyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxamide (137 mg) in N,N-dimethylformamide (1.5 mL) was added dropwise phosphoryl chloride (0.051 mL) under ice-cooling. This mixture was stirred for 50 minutes under ice-cooling. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (94.4 mg). 1H-NMR (CDCl3) δ ppm: 0.69-0.77 (2H, m), 0.92-1.03 (2H, m), 1.97-2.07 (1H, m), 4.46 (2H, s), 6.86 (1H, dd, J=1.5, 8.3 Hz), 7.11-7.17 (1H, m), 7.21-7.32 (2H, m), 7.33-7.64 (7H, m), 8.09 (1H, br s).

Provenance & Evidence