Hexane → 5'-(4-Fluorophenyl)-spiro[cyclohexane-1,3'-[3H]indol]-2'(1'H)-one 2'(O-benzyloxime)

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Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol), and 4-fluorophenyl boronic acid (0.72 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 (0.70 g, 1.7 mmol, 67%) as a viscous oil. 1H NMR (500 MHz, DMSO-d6) δ 1.42–1.77 (8H, m), 1.95–1.99 (2H, q), 5.00 (2H, s), 6.84 (1H, d, J=8.1 Hz), 7.21–7.63 (1H, m), 9.58 (1H, s); MS (ESI(−ve)) m/z 399 (M−H)−.

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