Hydrazine → HCID 178434364, compound

Temperature

165 °C

To a 150 mL sealed flask containing 50 mL dry ethylene glycol was dissolved 1-(2-bromo-5-fluoro-4-pyridinyl)ethanone (8.2 g, 37.6 mmol). Added dropwise via syringe next was anhydrous hydrazine (1.24 mL, 39.5 mmol). The stirred light yellow mixture was sealed, and heated at 165° C. After 3.5 h, the orange-tan reaction mixture was removed from heating. After cooling to room temperature, the contents were poured onto a stirring mixture of 300 g ice/water (1:1), wherein solid precipitation occurred. After stirring for 10 min, the off-white precipitate was collected. This solid was dried in vacuo and collected 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine as an off-white solid (7.9 g, 99%). ESI MS m/z=212 (M+1).

1. customTo a 150 mL sealed flask
2. additionAdded dropwise via syringe
3. customThe stirred light yellow mixture was sealed
4. customthe orange-tan reaction mixture was removed
5. temperaturefrom heating
6. temperatureAfter cooling to room temperature
7. additionthe contents were poured onto a stirring mixture of 300 g ice/water (1:1), wherein solid precipitation
8. customthe off-white precipitate was collected
9. customThis solid was dried in vacuo
10. customcollected 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine as an off-white solid (7.9 g, 99%)

ORD record

ord-a5fdc90a0ebb43c6bf08e05d643aacb7

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09260425B2