Pyridine, hydrofluoride (1:1) → HCID 66760222, compound

To a solution of 3-bromothieno[2,3-c]pyridin-7-amine (51 mg, 0.22 mmol) in pyridine hydrofluoride (1.2 mL) was added sodium nitrite (23.1 mg, 0.334 mmol). The reaction stirred at room temperature for 18 h. The reaction was then neutralized by addition of saturated aqueous sodium bicarbonate (40 mL). The mixture was extracted with ethyl acetate (2×10 mL). The combined organic fractions were washed with brine (1×20 mL), dried over sodium sulfate, filtered, and concentrated to afford 33 mg (59%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 8.20 (dd, J=5.6, 1.3 Hz, 1 H), 7.76 (s, 1 H), 7.62 (dd, J=5.6, 2.8 Hz, 1 H); MS (ESI): 232.04, 234.04 [M+H]+; HPLC tR=3.49 min (ZQ3, polar—4 min).

1. extractionThe mixture was extracted with ethyl acetate (2×10 mL)
2. washThe combined organic fractions were washed with brine (1×20 mL)
3. dry with materialdried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated

ORD record

ord-9d0cf7f79bf84a79914dca421276b4f5

Source dataset

uspto-grants-2013_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08378104B2