Acetonitrile → 2-(3-Bromopyridin-2-yl)acetonitrile

Temperature

-78 °C

Dry THF (100 mL) was cooled to −78° C. and n-butyllithium (2.5 M in hexanes; 23 mL, 58 mmol) was added. Acetonitrile (3.3 mL, 64 mmol) was added dropwise maintaining the temperature below −60° C. A white precipitate formed and the reaction mixture was stirred at −78° C. for 45 min. A solution of 2,3-dibromopyridine (2.0 g, 8.4 mmol) in dry THF (10 mL) was added dropwise and the reaction mixture stirred at −78° C. for 1.5 h then allowed to warm to room temperature. The reaction was quenched by the dropwise addition of water. The aqueous was extracted with DCM (×3) and the combined organics washed with brine, dried (MgSO4) and concentrated in vacuo. (3-Bromo-pyridin-2-yl)-acetonitrile (Intermediate 1) was purified by flash column chromatography.

1. temperaturemaintaining the temperature below −60° C
2. customA white precipitate formed
3. stirringthe reaction mixture stirred at −78° C. for 1.5 h
4. temperatureto warm to room temperature
5. customThe reaction was quenched by the dropwise addition of water
6. extractionThe aqueous was extracted with DCM (×3)
7. washthe combined organics washed with brine
8. dry with materialdried (MgSO4)
9. concentrationconcentrated in vacuo
10. custom(3-Bromo-pyridin-2-yl)-acetonitrile (Intermediate 1) was purified by flash column chromatography

ORD record

ord-08cbf2a9a0f241628a5c3fc2c7c6feab

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09241931B2