Sodium Carbonate → HCID 86663058, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-morpholinophenylboronic acid (5.0 g, 24 mmol), sodium carbonate (6.91 g, 65.2 mmol), tetrakistriphenylphosphine palladium (0) (1.40 g, 1.21 mmol), and methyl 3-amino-2,6-dibromoisonicotinate (7.86 g, 25 4 mmol) in a pressure flask was flushed with nitrogen. Toluene (60 mL) and methanol (20 mL) were added and the flask was sealed heated at 110° C. for 44 h. After cooling to RT, the solid was collected by filtration and washed with sat. aq. NaHCO3 solution, water, and dried to give methyl 3-amino-6-bromo-2-(4-morpholinophenyl)-isonicotinate (7.32 gm, 77%). MS (ESI) m/z 392.15 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 7.78 (1H, s), 7.58 (2H, d, J=8.85 Hz), 7.01 (2H, d, J=8.85 Hz), 6.00 (2H, br. s.), 3.94 (3H, s), 3.88-3.92 (4H, m), 3.22-3.28 (4H, m).

Provenance & Evidence