Benzenesulfonyl chloride → HCID 86703272, compound

Participants

Reaction Steps

To a solution of benzyl 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylate (3.04 g) in N,N-dimethylformamide (34 mL) was added sodium hydride (50 to 72% in oil, 342 mg) in one portion under ice-cooling. This mixture was stirred for 30 minutes under ice-cooling. Then, benzenesulfonyl chloride (1.04 mL) was added dropwise thereto, followed by stirring at room temperature for 4.5 hours. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine successively, 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 (1.10 g). 1H-NMR (CDCl3) δ ppm: 3.92 (3H, s), 4.09 (2H, s), 5.44 (2H, s), 6.62-6.68 (1H, m), 6.80 (1H, dd, J=2.4, 8.6 Hz), 7.21 (1H, d, J=8.6 Hz), 7.24-7.53 (16H, m), 7.85-7.93 (2H, m).

Provenance & Evidence