Ammonia → 5-Bromo-2-chloropyridine-3-carboxamide

Participants

Reaction Conditions

Reaction Steps

Sodium 5-bromo-2-chloronicotinate (229 mg, 0.798 mmol) was suspended in CH2Cl2 (7.9 mL). Oxalyl chloride (0.084 ml, 0.957 mmol) was added followed by DMF (0.002 mL, 0.080 mmol) and the reaction mixture was stirred at 23° C. for 1 h. The solvent was removed by evaporation and the intermediate residue was dried under vacuum for 90 minutes. The crude acid chloride was suspended in CH3CN (7.9 mL) and NH3 (7M in MeOH, 0.125 mL, 0.877 mmol) was added and the reaction mixture was stirred at ambient temperature for 16 h. The solvent was removed by evaporation and the residue was partitioned between EtOAc (20 mL) and H2O (20 mL). The EtOAc layer was removed and the aqueous layer was extracted with EtOAc (3×25 mL). The combined organics were washed with brine, dried over MgSO4 and concentrated. The resulting solid was triturated with cold CH2Cl2 to provide the desired product as a tan powder (80.5 mg, 43%). 1H NMR (CDCl3) δ 6.08 (s, 1H), 6.66 (s, 1H), 8.36 (d, 1H, J=2.54 Hz), 8.54 (d, 1H, J=2.54 Hz).

Provenance & Evidence