Potassium Carbonate → Methyl 3-amino-6-bromo-6'-morpholino-2,3'-bipyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine (400 mg, 1.379 mmol), methyl 3-amino-2,6-dibromoisonicotinate (427 mg, 1.379 mmol), tetra(triphenylphospine)palladium(0) (159 mg, 0.138 mmol), K2CO3 (762 mg, 5.51 mmol) in a microwave vial was flushed with nitrogen and DMF (4.0 mL) was added. The vial was sealed heated at 100° C. overnight. The reaction was diluted with EtOAc and water to give a precipitate. This was collected by filtration, washed with water and EtOAc to leave methyl 3-amino-6-bromo-6′-morpholino-2,3′-bipyridine-4-carboxylate (232 mg, 0.590 mmol, 42.8% yield) as a light green solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.49 (1H, d, J=1.76 Hz), 7.70-7.82 (2H, m), 6.71 (1H, d, J=8.81 Hz), 5.93 (2H, br. s.), 3.91 (3H, s), 3.76-3.86 (4H, m), 3.46-3.63 (4H, m).

Provenance & Evidence