Dimethylformamide → 5-(1-Ethylpiperidin-4-yloxy)-9H-dipyrido[2,3-b:4',3'-d]pyrrole-3,6-dicarbonitrile

Participants

Reaction Conditions

Reaction Steps

DMF (8 mL) was added to a mixture of 9-benzenesulfonyl-3-bromo-5-(1-ethyl-piperidin-4-yloxy)-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (200 mg, 0.37 mmol), zinc cyanide (217 mg, 1.85 mmol) and tetrakis(triphenylphosphine) palladium(0) (43 mg, 0.04 mmol) and the reaction mixture heated under microwave irradiation at 150° C. for 30 min. Triethylamine (2 mL) was then added and the reaction mixture heated at 50° C. for 24 h. The mixture was diluted with saturated aqueous sodium bicarbonate solution (100 mL) and extracted into 10% MeOH in DCM (2×25 mL). The combined organic phase was adsorbed onto HM-N then purified by flash chromatography (silica, 12 g column, ISCO, 0-10% MeOH in DCM) to afford the title compound as a cream solid (6 mg, 5%). 1H NMR (DMSO-D6, 400 MHz): 9.07 (d, J=2.0 Hz, 1H), 8.99 (d, J=1.9 Hz, 1H), 8.84 (s, 1H), 4.86-4.76 (m, 1H), 2.97-2.87 (m, 2H), 2.42 (q, J=7.2 Hz, 2H), 2.23-2.13 (m, 2H), 2.12-1.94 (m, 4H), 1.03 (t, J=7.2 Hz, 3H). LCMS (Method H): RT=5.27 min, M+H+=347.

Provenance & Evidence