Diisopropylamine → HCID 23506238, compound

Temperature

-60 °C

Diisopropylamine (5.1 g, 50 mmol) is dissolved in THF (100 ml), and thereto is added with stirring a solution of n-butyl lithium in hexane (27.3 ml, 45 mmol) at −70° C. Ten minutes thereafter, a solution of 3,5-dibromopyridine (10.0 g, 42 mmol) in THF (30 ml) is added dropwise over a period of time for 20 minutes during which the bulk temperature should not be raised over −60° C., and the mixture is further stirred for 5 minutes. Subsequently, 1-bromo-3-benzyloxypropane (10.0 g, 44 mmol) is added to the mixture, and the mixture is stirred at −70° C. for 2 hours. The mixture is warmed to 20° C. over a period of time for 2 hours. The reaction is quenched with a saturated brine (200 ml), and the mixture is extracted with ethyl acetate (300 ml×2). The extract is washed with a saturated brine (100 ml×2), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane) to give the title compound (9.0 g) as a pale yellow oil.

1. additionis added
2. stirringthe mixture is stirred at −70° C. for 2 hours
3. temperatureThe mixture is warmed to 20° C. over a period of time for 2 hours
4. customThe reaction is quenched with a saturated brine (200 ml)
5. extractionthe mixture is extracted with ethyl acetate (300 ml×2)
6. washThe extract is washed with a saturated brine (100 ml×2)
7. dry with materialdried over anhydrous magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customThe residue is purified by silica gel column chromatography (eluent: ethyl acetate/hexane)

ORD record

ord-f727b20f3f1f40b39111a8179c5a20fb

Source dataset

uspto-grants-2004_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06765095B2