Dichloromethane → HCID 67481451, compound

Temperature

90 °C

To a suspension of 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (0.50 g, 2.2 mmol), potassium vinyltrifluoroborate (0.34 g, 2.6 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II),complex with dichloromethane (1:1) (35 mg, 0.043 mmol) in 1-propanol (10 mL) was added triethylamine (0.30 mL, 2.2 mmol). The mixture was heated at 90° C. for 6 hours under an atmosphere of nitrogen. The mixture was cooled to room temperature and the volatiles were evaporated under reduced pressure. The residue was diluted with dichloromethane (50 mL) and filtered through a plug of diatomaceous earth. The filtrate was washed with 2N Hydrochloric acid (2×10 mL) and saturated aqueous sodium chloride, dried over magnesium sulfate, filtered and evaporated. The residue was purified via chromatography (silica gel column 24 g and 0%→2% methanol: dichloromethane). 2-Chloro-8-vinyl-[1,2,4]triazolo[1,5-a]pyridine was isolated as a white solid (0.336 g, 87%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.40 (d, J=6.8 Hz, 1H), 7.53 (d, J=7.3 Hz, 1H), 7.08-6.94 (m, 2H), 6.59 (d, J=17.6 Hz, 1H), 5.70 (d, J=11.2 Hz, 1H). MS=180, 182 (MH)+.

1. temperatureThe mixture was cooled to room temperature
2. customthe volatiles were evaporated under reduced pressure
3. additionThe residue was diluted with dichloromethane (50 mL)
4. filtrationfiltered through a plug of diatomaceous earth
5. washThe filtrate was washed with 2N Hydrochloric acid (2×10 mL) and saturated aqueous sodium chloride
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified via chromatography (silica gel column 24 g and 0%→2% methanol: dichloromethane)

ORD record

ord-c1f21cce135e415f97241fa4fc4aca02

Source dataset

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08633173B2