Sodium Carbonate → HCID 86663040, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chlorophenylboronic acid (3.03 g, 19.4 mmol), methyl 3-amino-2,6-dibromoisonicotinate (5.0 g, 16 1 mmol), tetrakistriphenylphosphine palladium (0) (1.12 g, 0.968 mmol), sodium carbonate (4.10 g, 38 7 mmol) was flushed with nitrogen, toluene (40 mL), and MeOH (13 mL) were added and the reaction was heated in a 93° C. for 30 hr. This was partitioned between EtOAc and water and the organic phase was washed with brine, dried with sodium sulfate, and the solvent removed. Silica gel chromatography (step gradient elution with DCM containing 75 to 0% hexane) afforded methyl 3-amino-6-bromo-2-(4-chlorophenyl)isonicotinate (3.86 g, 11 3 mmol, 70% yield) as a yellow fluffy solid. MS (ESI) m/z 343.02 (M+H). 1 H NMR (500 MHz, chloroform-d) δ ppm 7.81 (1H, s), 7.54-7.60 (2H, m), 7.43-7.49 (2H, m), 5.91 (2H, br.s.), 3.93 (3H, s).

Provenance & Evidence