Dimethylformamide → HCID 57721353, compound

Temperature

80 °C

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)+.

1. customThe excess SOCl2 was removed under reduced pressure
2. dissolutionThe residue dissolved in 50 mL of dichloromethane (DCM)
3. customThe two layers were separated
4. extractionthe aqueous layer extracted with EtOAc
5. washThe combined organic layers were washed with brine
6. dry with materialdried over MgSO4
7. filtrationAfter filtration and concentration
8. customthe residue was triturated with DCM
9. filtrationfiltered
10. washwashed with DCM

ORD record

ord-791254c87130471bae090d5f2ca2e93a

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07547782B2