Cesium fluoride → Methyl 3-amino-2-(4-(benzyloxy)phenyl)-6-bromoisonicotinate

Participants

Reaction Conditions

Reaction Steps

A flask containing a mixture of methyl 3-amino-2,6-dibromoisonicotinate (1000 mg, 3.23 mmol), 4-(benzyloxy)phenylboronic acid (883 mg, 3.87 mmol), cesium fluoride (1176 mg, 7.74 mmol) and tetrakis(triphenylphosphine)-palladium(0) (224 mg, 0.194 mmol) was flushed with nitrogen. Dimethoxyethane (16 mL) was added and the reaction was heated at 80° C. for 18 hr. The reaction was then partitioned between EtOAc and water. The organic phase was separated, washed with brine, dried with sodium sulfate, and the solvent removed. Radial silica gel chromatography (step gradient elution with hexane containing 30 to 20% methylene chloride) afforded 1055 mg of methyl 3-amino-2-(4-(benzyloxy)-phenyl)-6-bromoisonicotinate as a yellow solid. MS (ESI) m/z 415.1 (M+H). 1H NMR (CDCl3) δ ppm 7.77 (1H, s), 7.55 (2H, d, J=8.55 Hz), 7.31-7.46 (5H, m), 7.06 (2H, d, J=8.55 Hz), 5.95 (2H, br. s.), 5.12 (2H, s), 3.92 (3H, s).

Provenance & Evidence