HCID 86680498, compound → HCID 86680499, compound

Participants

Reaction Steps

In a hydrogenation apparatus, 2-(1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (800 mg, 1.9 mmol) and 5% palladium on carbon (151 mg) were combined. The reaction vessel was purged with nitrogen and 60 mL ethyl acetate, 15 mL ethanol, and 15 drops of concentrated HCl were added. The reaction vessel was pressurized with hydrogen gas to 50 psi. After 4 days, the apparatus was purged with nitrogen and the contents were filtered through celite. The Celite™ pad was washed with ethyl acetate to afford an orange solution. The solvent was removed on the rotovap and redissolved in dichloromethane. Silica gel (3.2 g) was added to the dichloromethane solution and the solvent was removed on the rotovap. The silica gel was transferred to the head of a chromatography column and eluted with 15% ethyl acetate in hexanes to afford 2-(1-(6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione and recovered 2-(1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. LC/MS (M+1, found=343.0). 1H NMR (400 MHz, CDCl3) δ 8.52 (s, 1H), 7.82 (m, 2H), 7.72 (m, 2H), 7.54 (d, J=5.9 Hz, 1H), 7.32 (d, J=5.9 Hz, 1H), 5.95 (q, J=7.0 Hz, 1H), 1.95 (d, J=7.0 Hz, 3H) ppm.

Provenance & Evidence