Dimethylformamide → HCID 57721353, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of 5-bromo-2-hydroxynicotinic acid (2.20 g, 10 mmol Synthesis, 2002, 528-532) in 10 mL of SOCl2 at room temperature was added slowly 1 mL of DMF and the resulting solution was then heated at 80° C. for 2 h. The excess SOCl2 was removed under reduced pressure. The residue dissolved in 50 mL of dichloromethane (DCM). To the mixture was added 2,4-di-fluoroaniline (1.29 g, 10 mmol), followed by the addition of 4 mL of triethylamine. The reaction mixture was stirred at room temperature for 1 h and then diluted with 20 mL of H2O. The two layers were separated and the aqueous layer extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. After filtration and concentration, the residue was triturated with DCM and filtered and washed with DCM to provide the desired compound (1.40 g, 40% yield). MS (ESI+) m/z 347.13, 349.12, 351.09 (M+H)+.

Provenance & Evidence