Reaktion #9431

Reaktionsgleichung

5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime)

3-Nitrophenyl boronic acid

→

desired compound

Ausbeute 55.0%

5′-(3-Nitrophenyl)-spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one 2′(O-benzyloxime)

Ausbeute 55.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigePurification by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate)

Vorschrift

Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3-Nitrophenyl boronic acid (0.86 g, 5.2 mmol) according to Example 45 procedure A. Purification by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate) afforded the desired compound (0.60 g, 1.4 mmol, 55%) as a viscous oil. 1H NMR (500 MHz, DMSO-d6) δ 1.42–1.82 (8H, m), 2.02–2.04 (2H, q), 5.01 (2H, s), 6.88 (1H, d), 7.28–7.71 (8H, m), 8.08–8.13 (2H, m), 8.38 (1H, d), 9.69 (1H, s); MS (ESI(−ve)) m/z 426 (M−H)−.

Quelle