Ammonium Hydroxide → HCID 66760410, compound

Participants

Reaction Steps

To a solution of thieno[2,3-c]pyridin-5-ylamine (24.0 mg, 0.160 mmol) in pyridine hydrofluoride (0.50 mL, 5.50 mmol) in a plastic bottle was added sodium nitrite (33.1 mg, 0.479 mmol). The reaction mixture was stirred at RT for 50 min. Another portion of sodium nitrite was added and the mixture was stirred at RT for another 30 min, then at 100° C. for 1 h. The reaction mixture was then poured into 1:1 NH4OH:water (10 mL) and extracted with EtOAc (3×15 mL). The combined organic extracts were washed with water (2×10 mL) and brine (10 mL), dried over MgSO4, and concentrated in vacuo. Purification by ISCO chromatography (0 to 30% EtOAc:heptane) afforded 8 mg (33%) of the title compound as a beige solid. 1H NMR (400 MHz, CDCl3): δ 8.75 (s, 1 H), 7.81 (d, J=5.6 Hz, 1 H), 7.35 (d, J=5.2 Hz, 1 H), 7.29-7.31 (m, 1 H); MS (ESI): 154.12 [M+H]+; HPLC tR=3.40 min (ZQ3: polar—5 min).

Provenance & Evidence