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

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was charged 3-iodo-4-(tetrahydro-2H-pyran-4-yloxy)-1-trityl-1H-pyrazolo[4,3-c]pyridine (1.00 g, 1.70 mmol), 2-chloropyridin-4-ylboronic acid (0.281 g, 1.79 mmol) and bis(diphenylphosphino)ferrocenepalladium chloride (139 mg, 0.170 mmol). Acetonitrile (11 mL, 210 mmol) and 1.0 M of potassium acetate in water (4.1 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 30 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 0-100% EtOAc in heptane to give the title compound (0.648 g, 66%). LC-MS (Method H): m/z=573.4 [M+H]+; 1.56 min. 1H-NMR (400 MHz, CDCl3): δ 8.37 (d, J=5.2, 1H), 8.13 (s, 1H), 7.80 (d, J=5.2, 1H), 7.54 (d, J=6.2, 1H), 7.35-7.27 (m, 9H), 7.22-7.14 (m, 6H), 5.90 (d, J=6.2, 1H), 5.55-5.46 (m, 1H), 4.01-3.92 (m, 2H), 3.69-3.60 (m, 2H), 2.23-2.13 (m, 2H), 1.99-1.87 (m, 2H).

Provenance & Evidence