Sodium Carbonate → HCID 86663044, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-isopropoxycarbonylphenylboronic acid (0.98 g, 4 7 mmol), sodium carbonate (1.02 g, 9.58 mmol), tetrakistriphenylphosphine palladium (0) (0.205 g, 0.177 mmol), and methyl 3-amino-2,6-dibromoisonicotinate (1.1 g, 3 6 mmol) in a vial was flushed with nitrogen. Toluene (12 mL) and methanol (4 mL) were added and the reaction stirred at 110° C. for 16 h. The reaction mixture was partitioned between EtOAc and sat. aq. sodium bicarbonate solution. The organic phase was washed with sat. aq. sodium bicarbonate solution, brine, and dried with sodium sulfate. Removal of the solvents followed by silica gel chromatography (step gradient elution with hexane containing 0 to 20% EtOAc afforded methyl 3-amino-6-bromo-2-(4-(isopropoxycarbonyl)phenyl)isonicotinate (1.04 g, 2.59 mmol, 73% yield). MS (ESI) m/z 393.00 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 8.14 (2H, d, J=8.24 Hz), 7.84 (1H, s), 7.69 (2H, d, J=8.24 Hz), 5.94 (2H, br. s.), 5.27 (1H, dt, J=12.51, 6.26 Hz), 3.93 (3H, s), 1.38 (6H, d, J=6.10 Hz).

Provenance & Evidence