Reaktion #715074

Reaktionsgleichung

3-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine

triphenylphosphine

potassium carbonate

N,N-dimethylformamide

→

4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine

Ausbeute 85.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated
2. 2
   Sonstigepartitioned between ethyl acetate and water
3. 3
   WaschenThe organic layer was washed with water and brine
4. 4
   Trocknendried over MgSO4
5. 5
   SonstigeThe crude product was purified on a silica gel column
6. 6
   Wascheneluting with 50% ethyl acetate in hexane

Vorschrift

3-Iodo-4-(2-(thiophen-3-yl)ethoxy)pyridine (1.66 g, 5.00 mmol), palladium acetate (112 mg, 0.500 mmol), triphenylphosphine (262 mg, 1.00 mmol) and potassium carbonate (1.38 g, 10.0 mmol) in N,N-dimethylformamide (80 mL, 1000 mmol) were heated at 115° C. for 2 hours. The reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with water and brine, and dried over MgSO4. The crude product was purified on a silica gel column eluting with 50% ethyl acetate in hexane to give 4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (yield 0.86 g, 85%). 1H NMR (400 MHz, CDCl3) δ 8.93 (s, 1H), 8.25 (d, J=5.5, 1H), 7.23 (d, J=5.2, 1H), 6.89 (dd, J=3.6, 5.3, 2H), 4.43-4.33 (m, 2H), 3.29-3.20 (m, 2H). MS (ESI+) 204.0

Quelle