Pyridine → HCID 532222, compound

Temperature

0 °C

To a stirred and 0° C. cooled solution of 4-bromoaniline (1.0 g, 5.8 mmol, 1.0 eq) and pyridine (0.61 mL, 7 mmol, 1.2 eq) in DCM (20 mL) was added drop wise a solution of 2,6-difluorobenzoyl chloride (0.8 mL, 6.4 mmol, 1.1 eq) in DCM (5 mL). After stirring the resulting mixture at the same temperature for 1 h, the solvent was removed under vacuum. The residue was taken into ethyl acetate (20 mL) and water (20 mL). The layers were separated. The aqueous layer was extracted with ethyl acetate (2×20 mL) and the combined organic layers were washed with brine (20 mL), dried (Na2SO4) and filtered. The filtrate was concentrated under vacuum to afford 1.20 g of the desired product as a white solid. 1HNMR (400 MHz, DMSO-d6) δ 7.78 (brs, 1H, D2O exchangeable), 7.53-7.37 (m, 5H), 7.02-6.95 (m, 2H); ESI-MS (m/z) 312, 314 [(MH)+ Br79,81].

1. stirringAfter stirring the resulting mixture at the same temperature for 1 h
2. customthe solvent was removed under vacuum
3. customThe layers were separated
4. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
5. washthe combined organic layers were washed with brine (20 mL)
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under vacuum

ORD record

ord-14c679d63a7d40dca479023d88144b58

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169242B2