Reaktion #9430

Reaktionsgleichung

hexane

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

3-methoxyphenyl boronic acid

→

desired product

Ausbeute 75.0%

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

Ausbeute 75.0%

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe product was purified by flash silica gel chromatography

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-methoxyphenyl boronic acid (0.79 g, 5.2 mmol) according to Example 45 procedure A. The product was purified by flash silica gel chromatography; (eluant: 10:0.5 hexane:ethyl acetate) to give the desired product (0.80 g, 1.9 mmol, 75%) as a viscous oil. 1H NMR (500 MHz, DMSO-d6) δ 1.43–1.78 (8H, m), 1.95–2.00 (2H, q), 3.80 (3H, s), 5.00 (2H, s), 6.82–6.86 (2H, m), 7.10–7.16 (2H, m), 7.28–7.53 (10H, m), 9.57 (1H, s); MS (ESI(−ve)) m/z 411 (M−H)−.

Quelle