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

Temperature

23 °C

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).

1. customThe solvent was removed by evaporation
2. customthe intermediate residue was dried under vacuum for 90 minutes
3. stirringthe reaction mixture was stirred at ambient temperature for 16 h
4. customThe solvent was removed by evaporation
5. customthe residue was partitioned between EtOAc (20 mL) and H2O (20 mL)
6. customThe EtOAc layer was removed
7. extractionthe aqueous layer was extracted with EtOAc (3×25 mL)
8. washThe combined organics were washed with brine
9. dry with materialdried over MgSO4
10. concentrationconcentrated
11. customThe resulting solid was triturated with cold CH2Cl2

ORD record

ord-5f478c29ef40416cacebb84fc504c6d5

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547782B2