p-Toluenesulfonic acid → HCID 86728243, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of compound 6-chloro-2-(4-fluoro-1H-indol-2-yl)pyridin-3-ol (60 mg, 0.224 mmol), thiophene-2-carbaldehyde (50 mg, 0.448 mmol) and PTSA (85 mg, 0.448 mmol) in toluene (1 mL) was stirred at 60° C. for 4 hours. The mixture was then diluted with water (20 mL) and extracted with EtOAc (15 mL*3). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using prep-TLC (petroleum ether:EtOAc=20:1) to provide 2-chloro-7-fluoro-6-(thiophen-2-yl)-6,11-dihydropyrido[2′,3′:5,6]pyrano[4,3-b]indole (40 mg, yield: 50.0%). 1H-NMR (CDCl3, 400 MHz) δ 9.28 (s, 1H), 7.07˜7.18 (m, 5H), 6.98 (d, J=8.4 Hz, 1H), 6.81˜6.86 (m, 2H), 6.66˜6.70 (m, 1H). MS (M+H)+: 357/359.

Provenance & Evidence