Sodium Carbonate → HCID 86663031, compound

Participants

Reaction Steps

A mixture of 4-(hydroxymethyl)phenylboronic acid (2.35 g, 15.5 mmol), methyl 3-amino-2,6-dibromoisonicotinate (4.0 g, 12.9 mmol), tetrakistriphenylphosphine palladium(0) (0.895 g, 0.774 mmol), sodium carbonate (3.28 g, 31.0 mmol) was flushed with nitrogen and toluene (32.3 mL), and MeOH (10.75 mL) were added. The reaction was heated at reflux under nitrogen for 24 hr. It was partitioned between EtOAc and water. The organic phase was washed with brine, dried with sodium sulfate, and the solvents removed. The organic phase was washed with brine, dried with sodium sulfate and the solvent removed. The residue was chromatographed (step gradient elution with DCM containing 0 to 20% EtOAc afforded methyl 3-amino-6-bromo-2-(4-(hydroxymethyl)phenyl)isonicotinate (1.99 g, 5.90 mmol, 46% yield) as a yellow fluffy solid. MS (ESI) m/z 336.8 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 7.80 (1H, s), 7.61 (2H, d, J=8.24 Hz), 7.48 (2H, d, J=7.93 Hz), 5.94 (2H, br. s.), 4.75 (2H, d, J=5.80 Hz), 3.92 (3H, s), 1.72 (1H, t, J=5.80 Hz).

Provenance & Evidence