Potassium Hydroxide → 3-(1-phenylsulfonyl-4-oct-1-enyl-1H-pyrazol-3-yl)-pyridine

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Reaction Steps

Compound 46C (0.35 g, 0.89 mmol), 0.7 g of KOH and 1 ml of NH2NH2.H2O were combined in diethylene glycol (10 ml) and warmed to reflux for 1 hour under N2. The mixture was cooled, concentrated and re-dissolved 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-oct-1-enyl-1H-pyrazol-3-yl)-pyridine (the deprotected analog of 46C). Yield 0.19 g (95%). 1H-NMR (400 MHz, CDCl3): δ 8.85 (d, J=2 Hz, 1H), 8.65 (dd, J=5 Hz, 2 Hz, 1H), 7.91 (dt, J=8 Hz, 2 Hz, 1H), 7.71 (s, 1H), 7.41-7.36 (m, 1H), 6.27 (d, J=16 Hz, 1H), 6.07-5.98 (m, 1H), 2.19-2.12 (m, 2H), 1.46-1.38 (m, 2H), 1.37-1.23 (m, 6H), 0.89 (t, J=7 Hz, 3H).

Provenance & Evidence