5-(1-Ethylpiperidin-4-yloxy)-3-isopropenyl-9H-dipyrido[2,3-b;4',3'-d]pyrrole-6-carbonitrile → 5-(1-Ethylpiperidin-4-yloxy)-3-isopropyl-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrile

Participants

Reaction Steps

A suspension of 5-(1-ethylpiperidin-4-yloxy)-3-isopropenyl-9H-dipyrido[2,3-b:4′,3′-d]pyrrole-6-carbonitrile (98 mg, 0.271 mmol), 10% palladium on carbon (50 mg) and triethylamine (0.5 mL) in IMS (5 mL) was stirred at ambient temperature under a hydrogen atmosphere for 18 h. The mixture was filtered through a PTFE filter and the filtrate concentrated in vacuo to give a brown solid. The resultant solid was purified by flash chromatography (silica, 12 g column, ISCO, 0-5% MeOH in DCM) to afford the title compound as a white solid (27 mg, 27%). 1H NMR (DMSO-D6, 300 MHz): 12.96 (s, 1H), 8.82 (s, 1H), 8.68 (s, 1H), 8.32 (s, 1H), 5.11-4.77 (m, 1H), 3.65-3.48 (m, 2H), 3.28-3.18 (m, 2H), 3.14-2.90 (m, 3H), 2.42-2.18 (m, 4H), 1.37 (d, J=6.9 Hz, 6H), 1.29-1.17 (m, 3H). LCMS (Method H): RT=7.10 min, M+H+=364.

Provenance & Evidence