Acetonitrile → 3-(2-Chloropyridin-4-yl)-4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was charged 3-iodo-4-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine (1.14 g, 2.21 mmol), 2-chloropyridin-4-ylboronic acid (0.366 g, 2.32 mmol) and bis(diphenylphosphino)ferrocenepalladium chloride (181 mg, 0.221 mmol). Acetonitrile (14 mL, 270 mmol) and 1.0 M of potassium acetate in water (5.3 mL) were then added and the reaction mixture was degassed with nitrogen for 10 minutes and then heated to 100° C. under microwave irradiation for 40 minutes. Upon reaction completion, the reaction mixture was diluted with dichloromethane, filtered through Celite® and concentrated in vacuo. The crude residue was purified by column chromatography eluting with 0-2% EtOAc in DCM to give the title compound (0.887 g, 80%). LC-MS (Method H): m/z=503.3 [M+H]+, 1.55 min. 1H-NMR (400 MHz, CDCl3): δ 8.38 (d, J=4.6, 1H), 8.06 (s, 1H), 7.86 (d, J=4.8, 1H), 7.58 (d, J=6.0, 1H), 7.35-7.28 (m, 9H), 7.23-7.14 (m, 6H), 5.91 (d, J=6.2, 1H), 4.11 (s, 3H.

Provenance & Evidence