Hydrazine → 4-Bromo-2-hydrazinyl-3-iodopyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromo-2-fluoro-3-iodopyridine (29 g, 96 mmol) in THF (300 mL) was added hydrazine (anhydrous, 30 mL, 960 mmol) at 20° C. The reaction mixture was stirred at 20° C. for 2 h. The reaction was monitored by HPLC (acetonitrile-water-TFA) and completed in 2 h. The reaction mixture was concentrated in vacuo to reduce volume by 70% and H2O (300 mL) was then added. The resulting mixture was filtered and the collected solid (1st crop) was washed with H2O. The filtrate was concentrated in vacuo to remove most of the THF. Newly formed solid was then filtered. This 2nd crop was washed with H2O. The two crops were combined and dried under high vacuum to obtain the title compound as an off-white, fluffy solid (28.6 g, 91 mmol). MS: [M+H]+=313.9. 1H NMR (400 MHz, CDCl3) δ 6.97 (d, J=5.50 Hz, 1H), 7.92 (d, J=4.95 Hz, 1H).

Provenance & Evidence