Microwave-assisted cross-coupling of 3-chloro-2-pyrazolines and 3-chloro-1-phenyl-1,4,5,6-tetrahydropyridazine with aryl boronic acids

Tetrahedron Letters

Volumn 46, Issue 15, 2005, Pages 2631-2634

  Wang, Hong Jun ^a   Keilman, Jeffrey ^a   Pabba, Chittari ^a   Chen, Zhen Jia ^a   Gregg, Brian T ^b  

^a ALBANY MOLECULAR RESEARCH INC   (United States)

^b ALBANY MOLECULAR RESEARCH INC   (United States)

Author keywords

1,4,5,6 Tetrahydropyridazine; 2 Pyrazoline; Boronic acids; Cross coupling; Microwave irradiation; Palladium

Indexed keywords

3 CHLORO 1 PHENYL 1,4,5,6 TETRAHYDROPYRIDAZINE; 3 CHLORO 1 PHENYL 2 PYRAZOLINE; BORONIC ACID DERIVATIVE; PYRAZOLINE DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; MICROWAVE RADIATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE DEPENDENCE;

EID: 15244357888     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.02.075     Document Type: Article

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36. 3 (15 mmol, 1.4 mL) in toluene (20 mL) was heated at 70°C for 1-2 h (monitored by TLC). After cooling to room temperature, the reaction mixture was slowly poured into a solution of sodium bicarbonate (50 mmol, 4.2 g) in ice water (100 mL), and extracted with methylene chloride (2 × 40 mL). The organic layers were combined, washed with brine (30 mL), diluted with hexane (80 mL), dried over sodium sulfate, and filtered through a pad of silica gel (40 mL). The silica gel was further eluted with 10% ethyl acetate/hexanes (100 mL). The organics were combined, and evaporated under vacuum to give the product, which was used in the cross-coupling reactions without further purification
37. 4 (17.3 mg, 0.015 mmol), and acetonitrile (1.2 mL). The vial was sealed without degassing, and the suspension was heated at 140°C for 5 min (fixed hold time) in the Smithcreator. The reaction mixture was partitioned between methylene chloride (40 mL) and water (20 mL). The organic layer was washed with brine (20 mL), dried over sodium sulfate, and filtered through Celite. The solvent was evaporated under vacuum, and the resulting crude product was purified by preparative TLC or flash chromatography