Sodium Carbonate → HCID 86663036, compound

Participants

Reaction Steps

A flask containing a mixture of 3-(hydroxymethyl)phenylboronic acid (0.88 g, 5.79 mmol), methyl 3-amino-2,6-dibromoisonicotinate (1.5 g, 4 8 mmol), tetrakistriphenylphosphine Pd(0) (0.335 g, 0.290 mmol), sodium carbonate (1.23 g, 11.6 mmol) was flushed with nitrogen and toluene (12 mL), and MeOH (4 mL) were added. The reaction was heated at reflux under nitrogen for 48 hr. It was partitioned between EtOAc and water and the organic phase was separated, washed with brine, dried with sodium sulfate, and the solvent removed. Chromatography (step gradient elution with DCM containing 0 to 15% EtOAc) afforded methyl 3-amino-6-bromo-2-(3-(hydroxymethyl)phenyl)isonicotinate (1.4 g, 4.2 mmol, 86% yield) as a yellow solid. MS (ESI) m/z 339.02 (M+H). 1H NMR (400 MHz, chloroform-d) δ ppm 7.80 (1H, s), 7.58 (1H, s), 7.40-7.55 (3H, m), 5.94 (2H, br. s.), 4.74 (2H, d, J=5.79 Hz), 3.92 (3H, s), 1.77 (1H, t, J=5.92 Hz).

Provenance & Evidence