Reaktion #66250

Reaktionsgleichung

ethyl 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate

phenyl boronic acid

pyridine

→

title compound

Ausbeute 7.9%

3-Phenyl-1,2,3,4,5,6-Hexahydro-Azepino[4,5-b]Indole-5-Carboxylic Acid Ethyl Ester

Ausbeute 7.9%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe mixture was filtered though a pad of celite
2. 2
   EinengenThe filtrate was concentrated in vacuo
3. 3
   Sonstigepurified by chromatography on silica gel eluting with EtOAc-Hexane (7:93)

Vorschrift

The mixture of ethyl 1,2,3,4,5,6-hexahydroazepino[4,5-b]indole-5-carboxylate (520 mg, 2 mmol), cupric acetate (728 mg, 4 mmol), phenyl boronic acid (490 mg, 4 mol) and pyridine (0.35 mL, 4 mmol) in dry DCM (20 mL) was stirred at ambient temperature for 3 days. The mixture was filtered though a pad of celite. The filtrate was concentrated in vacuo and then purified by chromatography on silica gel eluting with EtOAc-Hexane (7:93) to give the title compound (53 mg); 1H-NMR (CDCl3): δ 8.66 (1H, s), 7.42 (1H, d), 7.26-7.18 (4 h, m), 7.10-7.00 (2H, m), 7.69 (2H, m), 6.67 (1H, t), 5.22 (1H, m), 4.40-4.18 (3H, m), 4.04-4.01 (1H, m), 3.98-3.88 (1H, m), 3.58-3.52 (1H, m), 3.22-3.15 (1H, m), 3.08-3.02 (1H, m), 1.27 (3H, t); MS (ES): 335 (MH+).

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