Phosphorus oxybromide → 4-Bromo-2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridine

Temperature

100 °C

To a stirred solution of 2-(2-chloro-6-fluorophenyl)thiazolo[5,4-c]pyridin-4(5H)-one (0.30 g, 1.1 mmol) in MeCN (50 mL), was added POBr3 (0.92 g, 3.2 mmol). The mixture was heated at 100° C. for 2 hours and then cooled to room temperature. The reaction was quenched with ice and extracted with EtOAc (3×20 mL). The combined organic extract was washed with saturated NaHCO3 solution (100 mL) and brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography eluting with a 0-10% gradient of EtOAc in petroleum ether to give the desired product as a white solid (0.22 g, 60% yield). 1H NMR (500 MHz, DMSO-d6): δ 8.59 (d, J=5.5 Hz, 1H), 8.27 (d, J=5.5 Hz, 1H), 7.76-7.68 (m, 3H). LCMS (ESI) m/z: 342.9 [M+H+].

1. temperaturecooled to room temperature
2. customThe reaction was quenched with ice
3. extractionextracted with EtOAc (3×20 mL)
4. extractionThe combined organic extract
5. washwas washed with saturated NaHCO3 solution (100 mL) and brine (100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel column chromatography
9. washeluting with a 0-10% gradient of EtOAc in petroleum ether

ORD record

ord-02a5a1fbbfcd474c9cf06d400143b2c5

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697708B2