Reaktion #9432

Reaktionsgleichung

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

3-cyanophenyl boronic acid

→

desired product

Ausbeute 71.0%

5′-(3-CYANOPHENYL)SPIRO[CYCLOHEXANE-1,3′-[3H]INDOL]-2′(1′H)-ONE OXIME

Ausbeute 71.0%

Lösungsmittel

benzonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe product was purified by flash silica gel chromatography (eluant: 10:0.5 hexane:ethyl acetate)

Vorschrift

3-[Spiro[cyclohexane-1,3′-[3H]indol]-(1′H)-one-2′-(O-benzyloxime)]benzonitrile[3H]indol]-5-yl]benzonitrile. Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3-cyanophenyl boronic acid (0.76 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 (0.75 g, 1.8 mmol, 71%) as a viscous oil. 1H NMR (500 MHz, DMSO-d6) δ 1.41–1.81 (8H, m), 1.96–2.03 (2H, q), 5.01 (2H, s), 6.86 (1H, d), 7.28–7.33 (9H, m), 7.95–7.97 (1H, d), 8.12 (1H, s), 9.65 (1H, s); MS (ESI(−ve)) m/z 406 (M−H)−.

Quelle