Triphenylphosphine → 2-(5-Chloropyridin-2-yl)-2,2-difluoroethan-1-amine

To a solution of 2-(2-Azido-1,1-difluoro-ethyl)-5-chloro-pyridine (1.94 g, 8.87 mmol) (prepared essentially as described for Example 14b) in THF (30 mL) cooled in an ice bath were added triphenylphosphine pellets (2.6 g, 9.76 mmol). The mixture was stirred at room temperature for 16 h. Ammonium hydroxide solution (10 mL) was added to the mixture followed by additional stirring for 4 h. NaOH solution (3 N, 40 mL) was then added and the mixture was heated at 40° C. for 1 h. The organic layer was separated and washed with HCl solution (2 N, 60 mL). The aqueous layer was then basified with 4 N NaOH solution and extracted with EtOAc twice. The solvent was evaporated to leave a pale yellow oil (1.6 g, 93% yield). 1H NMR (300 Hz, CDCl3) δ 8.59 (d, 1H), 7.78 (dd, 1H), 7.62 (d, 1H), 3.40 (t, 2H); LC/MS (m/z) [M+1]+ 193.0 (calculated for C7H7ClF2N2, 192.0).

1. temperaturecooled in an ice bath
2. stirringby additional stirring for 4 h
3. temperaturethe mixture was heated at 40° C. for 1 h
4. customThe organic layer was separated
5. washwashed with HCl solution (2 N, 60 mL)
6. extractionextracted with EtOAc twice
7. customThe solvent was evaporated

ORD-Eintrag

ord-62fcd205c3684cdfb7ff75622e628822

Quelldatensatz

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07550474B2