Potassium Carbonate → HCID 67125893, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was charged with methyl 5-bromopicolinate (250 mg, 1.22 mmol), tert-butyl 4-(4,4,5,5-tetramethyl-1,3-dioxolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (393 mg, 1.34 mmol), K2CO3 (400 mg, 3.03 mmol), and 3 mL of DMF. The vial was then flushed with argon while PdCl2(dppf)2 (42 mg, 0.060 mmol) was added. The resulting mixture was then capped and heated at 140° C. for 10 min in a microwave reactor. LC-MS indicated that the reaction was complete. The reaction mixture was then partitioned between EtOAc (25 mL) and water (10 mL). The organic layer was washed with brine (10 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to give an oil which was purified by silica gel column chromatography, eluting with 0-60% EtOAc in hexanes, to give methyl 5-(1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)picolinate (250 mg, 68%). LC-MS (ESI) m/z 319 (M+H)+.

Provenance & Evidence