Hydrazine hydrate (1:1) → HCID 66632471, compound

Participants

Reaction Conditions

Reaction Steps

2-(1-(6-(Pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (220 mg, 0.57 mmol) was slurried in ethanol (5 mL). To this slurry was added hydrazine hydrate (500 uL, 10.3 mmol, 18 eq). The reaction was heated to 60° C. for 2 h, then cooled to rt and filtered. The filtrate was concentrated and redissolved in ethyl acetate and water. The layers were separated and the organic layer was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to afford 1-(6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)-ethanamine (134 mg, 91.9% yield). 1H NMR (400 MHz, CDCl3) δ 8.69 (ddd, J=4.7, 1.6, 0.8 Hz, 1H), 8.39 (s, 1H), 7.87 (m, 2H), 7.57 (d, J=5.9 Hz, 1H), 7.34 (ddd, J=6.8, 5.1, 2.0, 1H), 7.31 (d, J=5.9 Hz, 1H), 4.63 (q, J=6.7 hz, 1H), 1.44 (d, J=6.7 Hz, 3H) ppm.

Provenance & Evidence