Potassium Hydroxide → 3-(1-Phenylsulfonyl-4-[2-(3-fluoro-phenyl)-vinyl]-1h-pyrazol-3-yl)-pyridine

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Reaction Steps

Compound 46B (1.06 g, 2.62 mmol), 1.3 g of KOH and 2 ml NH2NH2.H2O were combined in diethylene glycol (25 ml) and warmed to reflux for 1 hour under N2. The mixture was cooled, concentrated and redissolved in MeOH. Filtration over 25 g of SCX-2 (MeOH followed by 1 N NH3/MeOH) and subsequent purification by flash chromatography (ethyl acetate) afforded 3-{4-[2-(3-fluor-phenyl)-vinyl]-1H-pyrazol-3-yl}-pyridine (the deprotected analog of 46B). Yield 0.42 g (60.4%). 1H-NMR (400 MHz, CDCl3): δ 8.85 (d, J=2 Hz, 1H), 8.65 (dd, J=5 Hz, 2 Hz, 1H), 7.95-7.90 (m, 2H), 7.45-7.41 (m, 1H), 7.32-7.27 (m, 1H), 7.20-7.16 (m, 1H), 7.14-7.09 (m, 1H), 6.99 (d, J=16 Hz, 1H), 6.96-6.86 (m, 2H).

Provenance & Evidence