Réaction #9429

Équation de réaction

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

3,4-diflurophenyl boronic acid

→

desired product

Rendement 69.0%

5′-(3,4-Difluorophenyl)-spiro[cyclohexane-1,3′-[3H]indol]-2′(1′H)-one 2′(O-benzyloxime)

Rendement 69.0%

Solvants

THF water

Conditions de réaction

Traitement

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

Mode opératoire

Prepared from 5′-bromospiro{cyclohexane-1,3′-[3H]indol}-2′(1′H)-one 2′(O-benzyloxime) (1.0 g, 2.6 mmol) and 3,4-diflurophenyl boronic acid (1.6 g, 5.2 mmol of a 50% solution of acid in THF/water) 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, 1.7 mmol, 69%) as a viscous oil. 1H NMR (500 MHz, DMSO-d6) δ 1.41–1.78 (8H, m), 1.95–1.99 (2H, q), 5.00 (2H, s), 6.82 (1H, d), 7.28–7.46 (8H, m), 7.58 (1H, q), 7.67–7.71 (1H, m), 9.61 (1H, s); MS (ESI(−ve)) m/z 417 (M−H)−.

Source