Efficient fluoride-mediated synthesis of 5-alkyl amino- and ether-substituted pyrazoles

Tetrahedron Letters

Volumn 46, Issue 40, 2005, Pages 6887-6891

  Shavnya, Andrei ^a   Sakya, Subas M ^a   Minich, Martha L ^a   Rast, Bryson ^a   DeMello, Kristin Lundy ^a   Jaynes, Burton H ^a  

^a PFIZER INC   (United States)

Author keywords

COX 2 inhibitors; Fluoride mediated; Pyrazoles

Indexed keywords

1 (4 METHYLSULFONYL 2 PYRIDYL) 5 CHLORO 4 CYANO PYRAZOLE DERIVATIVE; 5 ETHER PYRAZOLE DERIVATIVE; FLUORIDE; PYRAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 27744501831     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.08.022     Document Type: Article

References (25)

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24. Sample reaction procedure: 5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3- trifluoromethyl-1H-pyrazole-4-carbonitrile (351 mg, 1 mmol) and (4-methylene-cyclohexyl)-methanol (252 mg, 2 mmol) were dissolved in dry dimethylsulfoxide (DMSO) (5 mL) and potassium fluoride (116 mg, 2 mmol) was added to the mixture. The resulting mixture was stirred at 20 °C for a period of 48 h. Analytical HPLC indicated the reaction completion. The reaction mixture was poured into water (15 mL) and the resulting mixture was extracted with ethyl acetate (2 × 20 mL). The organic extract was dried over magnesium sulfate and concentrated with a rotary evaporator. The desired product 9e (299 mg, 68%) was isolated by chromatography on silica gel column (Flash 40M; 15% EtOAc:15% acetone in hexane). MS (m/z): 441 (M+H); retention time (rt): 3.0 min.
25. 6) 155.9, 154.2, 148.2, 139.6, 119.2, 113.2, 113.1, 112.0, 109.9, 79.0, 71.6, 55.9, 44.3, 18.9 ppm.