Potassium Carbonate → 5-bromothieno[2,3-b]pyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([Si](C)(C)C)[S:8][C:5]2=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][S:8][C:5]2=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
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).