Hydrazine → 2-Bromo-6-hydrazinopyridine

To a solution of 2-bromo-6-fluoropyridine (2-1) (1.0 g, 5.68 mmol) in THF (10 mL) was added hydrazine (0.91 g, 0.89 mL, 28.4 mmol). After stirring for 1 h room temperature, the mixture was heated at 65° C. for 1 h. The mixture was cooled, diluted with EtOAc (200 mL), washed with water (10 mL) and brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. The resulting crude product (2-2) was used in the subsequent step without further purification. 1H NMR (300 MHz, CHCl3-d): δ 7.32 (app t, J=7.8 Hz, 1H), 6.82 (dd, J=7.8, 0.6 Hz, 1H), 6.67 (dd, J=7.8, 0.6 Hz, 1H), 5.93 (s, 1H), 3.80 (s, 2H).

1. temperaturethe mixture was heated at 65° C. for 1 h
2. temperatureThe mixture was cooled
3. washwashed with water (10 mL) and brine (10 mL)
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customThe resulting crude product (2-2) was used in the subsequent step without further purification

ORD record

ord-58a92409a42d4d24a36b46031f341c31

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266881B2