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

Temperature

100 °C

To a stirred solution of 2-(2,6-dichlorophenyl)thiazolo[5,4-c]pyridin-4(5H)-one (0.32 g, 1.1 mmol) in CH3CN (50 ml) was added POBr3 (0.918 g, 3.21 mmol). The mixture was heated at 100° C. for 2 hours. The mixture was cooled to room temperature, quenched with ice (200 mL) and extracted with EtOAc (3×20 mL). The combined organic extract was washed with saturated NaHCO3 (100 mL) and brine (100 mL), dried over Na2SO4, and concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography eluting with a 0-10% gradient of EtOAc/petroleum ether to give the desired product as a white solid (0.22 g, 56% yield). 1H NMR (500 MHz DMSO-d6): δ 8.59 (d, J=5.5 Hz, 1H), 8.26 (d, J=6.0 Hz, 1H), 7.76-7.74 (m, 2H), 7.71-7.68 (m, 1H). LCMS (ESI) m/z: 359.1 [M+H+].

1. temperatureThe mixture was cooled to room temperature
2. customquenched with ice (200 mL)
3. extractionextracted with EtOAc (3×20 mL)
4. extractionThe combined organic extract
5. washwas washed with saturated NaHCO3 (100 mL) and brine (100 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe resultant residue was purified by silica gel column chromatography
9. washeluting with a 0-10% gradient of EtOAc/petroleum ether

ORD record

ord-42fd5f946c08490a90db98fffe8e8462

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697708B2