1,2-Dibromoethane → 1-(6-Bromopyridin-2-YL)cyclopropanecarbonitrile

Temperature

0 °C

n-Butyllithium (6.66 ml, 10.7 mmol) was added to a cooled (0° C.) solution of diisopropylamine (1.52 ml, 10.7 mmol) in THF (10 mL) and maintained at 0° C. for 30 minutes. The reaction was then cooled to −78° C. and a solution of (6-bromopyridin-2-yl)acetonitrile (Example 235, Step 1) (1 g, 5.08 mmol) in tetrahydrofuran (10 mL) was added dropwise. The reaction was maintained at −78° C. for 1 hour, and then 1,2-dibromoethane (0.92 ml, 10.7 mmol) was added. The reaction was allowed to warm to room temperature and maintained at room temperature for 3 days. The mixture was then diluted with water and ethyl acetate and the layers were separated. The organic layer was dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography afforded the title compound.

1. temperatureThe reaction was then cooled to −78° C.
2. temperatureThe reaction was maintained at −78° C. for 1 hour
3. temperatureto warm to room temperature
4. temperaturemaintained at room temperature for 3 days
5. customthe layers were separated
6. dry with materialThe organic layer was dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customPurification by silica gel chromatography

ORD record

ord-8105fbe7f4cc49b7b24d5d28a2c262f1

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08367706B2