Reaktion #1094745

Reaktionsgleichung

water

5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbonitrile

(2-fluoro-phenyl)-methanethiol

cesium fluoride

→

desired product

Ausbeute 83.0%

5-(2-Fluoro-benzylsulfanyl)-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbonitrile

Ausbeute 83.0%

Lösungsmittel

DMSO

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with ethyl acetate (20 ml)
2. 2
   ExtraktionThe organic extract
3. 3
   Trocknenwas dried over magnesium sulfate
4. 4
   Einengenconcentrated with a rotary evaporator

Vorschrift

5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbonitrile (0.512 g, 1.46 mmol) and (2-fluoro-phenyl)-methanethiol (0.415 g, 2.92 mmol) were dissolved in dry DMSO (5 ml) and cesium fluoride (0.154 g, 2.92 mmol) was added to the clear solution. The resulting mixture was stirred at 20° for a period of 48 hours. Analytical HPLC indicated the reaction completion. The reaction mixture was poured into water (50 ml) and the resulting mixture was extracted with ethyl acetate (20 ml). The organic extract was dried over magnesium sulfate and concentrated with a rotary evaporator. The desired product (0.55 g, 83%) was isolated by chromatography on silica gel eluting with a gradient (from 20-40%) of ethyl acetate in hexane. MS: 457, r.t.: 27, 1H-NMR (CDCl3, 400 MHZ) δ 9.05 (d, 1H, H—Ar), 8.44-8.41 (q, 1H, H—Ar), 8.05 (d, 1H, H—Ar), 7.34-7.27 (m, 2H, H—Ar), 7.13-7.02 (m, 2H, H—Ar), 4.61 (s, 2H, CH2 of the benzyl group), 3.16 (s, 3H, CH3 of the CH3SO2 group) ppm.

Quelle