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, 1.59M hexane solution) at −78° C. and the mixture was stirred for 10 minutes. Then, 3-chloropyridine (1.13 g, 10 mmol) was added to the resulting mixture. Thirty minutes later, 2,5-difluorobenzaldehyde (1.09 ml, 10 mmol) was added to the mixture. The mixture was warmed gradually to 0° C., at which stirring was conducted for further 10 minutes. An aqueous solution of ammonium chloride was added and the mixture was diluted with ethyl acetate (80 ml). The organic layer obtained by separation was washed with brine and then dried. After filtration, the filtrate was concentrated under reduced pressure. The precipitate thus obtained was triturated with ethanol to yield the title compound (1.33 g, 52%).

1. stirringstirring
2. waitwas conducted for further 10 minutes
3. customThe organic layer obtained by separation
4. washwas washed with brine
5. customdried
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customThe precipitate thus obtained
9. customwas triturated with ethanol

ORD record

ord-bf834087c8954c5c9fdbd021d4c243e3

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07399775B2