Potassium Carbonate → 5-bromothieno[2,3-b]pyridine

Temperature

65 °C

The 5-bromo-2-(trimethylsilyl)thieno[2,3-b]pyridine from Part A (8.99 g, 31.4 mmol) was dissolved in ethanol (70 mL), followed by addition of K2CO3 (10.85 g, 78.5 mmol). Reaction was stirred at 65° C. for 1 hour. The reaction mixture was allowed to cool to 25° C., concentrated to dryness, and dissolved in EtOAc (150 mL). The solution was washed with H2O (80 mL), and brine (150 mL), dried over Na2SO4, filtered, and concentrated to yield white solid, 5-bromothieno[2,3-b]pyridine, 6.57 g (98%). 1H NMR (300 MHz, CDCl3) δ 8.60 (d, J≦2.2 Hz, 1H), 8.16 (d, J=2.2 Hz 1H), 7.57 (d, J=6.0 Hz 1H), 7.21 (d, J=6.0 Hz, 1H).

1. customReaction
2. temperatureto cool to 25° C.
3. concentrationconcentrated to dryness
4. dissolutiondissolved in EtOAc (150 mL)
5. washThe solution was washed with H2O (80 mL), and brine (150 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-6fc6a89b83e442d4b3ce603f2118a6fa

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08591943B2