Acetonitrile → HCID 583430, compound

Temperature

78 °C

To a solution of anhydrous acetonitrile (10.1 mL, 191.83 mmol, 3.3 equiv.) in dry THF (500 mL) was added dropwise n-butyl lithium (2.5 M in hexane, 69.8 mL, 174.39 mmol, 3 equiv.) at minus 78° C. under a nitrogen atmosphere. The resulting white suspension was stirred at minus 78° C. for 1 hour, and then a solution of 2-bromo-5-methylpyridine (10.0 g, 58.13 mmol, 1 equiv.) in dry THF (30 mL) was added. The reaction mixture was kept at minus 78° C. for 1 hour and then warmed up slowly to room temperature and stirred for another hour. Ice/water was added and the layer was separated. The organic layer was washed with water and brine, dried over MgSO4, filtered, and evaporated to give 18 g of crude product, which was used for next step reaction without further purification.

1. waitThe reaction mixture was kept at minus 78° C. for 1 hour
2. temperaturewarmed up slowly to room temperature
3. stirringstirred for another hour
4. customthe layer was separated
5. washThe organic layer was washed with water and brine
6. dry with materialdried over MgSO4
7. filtrationfiltered
8. customevaporated

ORD record

ord-d7422f1657ff4116a13a557165c0f1d5

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318947B2