Diisopropylamine → 3-Chloro-4-[(2,5-difluorophenyl)-hydroxymethyl]pyridine

Temperature

0 °C

To a tetrahydrofuran solution (14 ml) of diisopropylamine (1.4 ml, 10 mmol) was added n-butyl lithium (6.3 ml, a 1.59M hexane solution) at −78° C. After the resulting mixture was stirred for 10 minutes, 3-chloropyridine (1.13 g, 10 mmol) was added thereto. Thirty minutes later, 2,5-difluorobenzaldehyde (1.09 ml, 10 mmol) was added and the temperature of the resulting mixture was raised gradually to 0° C. Stirring was conducted for further 10 minutes. After addition of an aqueous solution of ammonium chloride, the resulting mixture was diluted with ethyl acetate (80 ml). The organic layer was separated, washed with brine and then dried. After filtration, the precipitate obtained by concentrating the resulting solution under reduced pressure was triturated with ethanol to give the title compound (1.33 g, 52%).

1. customat −78° C
2. stirringStirring
3. waitwas conducted for further 10 minutes
4. customThe organic layer was separated
5. washwashed with brine
6. customdried
7. filtrationAfter filtration
8. customthe precipitate obtained
9. concentrationby concentrating the resulting solution under reduced pressure
10. customwas triturated with ethanol

ORD record

ord-f4d0c88175014927b6534a4f8807326a

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932271B2