Reaktion #802346

Reaktionsgleichung

2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

2-bromothiophene

K3PO4

L-Proline

→

2,8-dimethyl-5-thiophen-2-yl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

Ausbeute 3.5%

Lösungsmittel

water

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with EtOAc
2. 2
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   Sonstigeto afford crude material, which
5. 5
   Sonstigewas purified by reverse phase HPLC

Vorschrift

A solution of 2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.4 g, 2 mmol), 2-bromothiophene (0.347 mL, 4 mmol), K3PO4 (0.848 g, 4 mmol), CuI (38 mg, 0.2 mmol) and L-Proline (46 mg, 0.39 mmol) in dry DMF (6 mL) was stirred at 150° C. for 16 h. The reaction mixture was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford crude material, which was purified by reverse phase HPLC to yield 2,8-dimethyl-5-thiophen-2-yl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (20 mg). 1H NMR (TFA salt, CD3OD) d (ppm): 7.50 (d, 1H), 7.30 (s, 1H), 7.15 (m, 3H), 7.05 (d, 1H), 4.78 (m, 1H), 4.39 (m, 1H), 3.80 (m, 1H), 3.58 (m, 1H), 3.15 (s, 3H), 3.05 (m, 2H), 2.42 (s, 3H).

Quelle