491875-99-1

Upstream product

• 867203-96-1 3-(4-fluorophenyl)-5-iodomethylisoxazoline 
• 49750-46-1 p-fluorobenzonitrile oxide 
• 106-96-7 propargyl bromide 
• 393165-20-3 (Z)-N-hydroxy-4-fluoro-benzenecarboximidoyl chloride 
• 833462-37-6 3-(4-fluorophenyl)-5-[(phenylselanyl)methyl]-4,5-dihydroisoxazole 
• 42202-95-9 4-fluoro-N-hydroxybenzimidoyl chloride 
• 459-23-4 4-fluorobenzaldoxime 
• 329-79-3 1-(4-fluorophenyl)ethanone oxime 
• 1736-21-6 3-(4-fluoro-phenyl)-5-methyl-isoxazole-4-carboxylic acid 
• 61668-02-8 1-(4-fluorophenyl)but-3-en-1-one 
• 459-57-4 4-fluorobenzaldehyde 
• 86718-78-7 1-(4-fluorophenyl)-3-buten-1-ol 
• 904672-47-5 1-(4-fluorophenyl)but-3-en-1-one oxime 

Downstream Products

• 491876-02-9 C₁₀H₉BFNO₃ 
• 491876-00-7 4-bromo-3-(4-fluorophenyl)-5-methyl-isoxazole 

Relevant academic research and scientific papers

Oxime-mediated facile access to 5-methylisoxazoles and applications in the synthesis of valdecoxib and oxacillin

A palladium-catalyzed efficient synthesis of 5-methylisoxazoles via oxime-mediated functionalization of unactivated olefins is described. The reaction affords a variety of 5-methylisoxazoles in moderate to good yields. To further demonstrate the utility of the method, the rapid synthesis of valdecoxib and oxacillin is reported. (Chemical Equation Presented).

Pd(0)-catalyzed decarboxylative coupling and tandem C-H arylation/decarboxylation for the synthesis of heteroaromatic biaryls

An effective Pd(0) carbene complex was successfully employed in the decarboxylative coupling of the heteroaromatic carboxylic acids (imidazo[1,2-a]pyridine and isoxazole) with aryl halides. For carboxyindoles, either decarboxylative coupling or tandem C-H arylation and decarboxylation occurred, leading to the formation of C2-monoarylated indoles.

Reaction of allenylmagnesium and allenylindium bromides with nitrile oxides: synthesis of novel 5-butynyl- and 5-methylisoxazoles

5-Butynylisoxazoles were obtained in high yields through a domino addition, C-O heterocyclization involving allenylmagnesium bromide and benzonitrile oxide in dry THF, in which the corresponding 5-methylisoxazoles were isolated in trace amounts. However, when the reactions were attempted in aqueous media using allenylindium bromide, 5-methylisoxazoles were formed as the sole products in high yields.

Preparation of isoxazol(in)yl substituted selenides and their further deselenenylation reaction to synthesize 3,5-disubstituted isoxazoles

We report a mild 1,3-dipolar cycloaddition protocol for the preparation of 3-aryl-5-phenylselenomethyl isoxazoles and isoxazolines regioselectively. The former was further reacted with LDA and electrophilic substrates followed by selenoxide syn-eliminatio

Convenient Approach to 3,4-Diarylisoxazoles Based on the Suzuki Cross-Coupling Reaction

The Suzuki cross-coupling reaction was found effective for rapid access to a series of 3,4-diarylisoxazoles of pharmacological interest. The efficiency of this approach was demonstrated by the synthesis of the highly potent COX-2-selective inhibitor, 4-(5-methyl-3-phenyl-4-isoxazolyl)benzenesulfonamide (valdecoxib), and its analogues. Thus, the coupling reaction between (3-aryl-5-methyl-4-isoxazolyl)boronic acids, prepared in situ from the corresponding bromides using triisopropyl borate, and aryl bromides containing a 4-sulfonamide or 4-methylsulfonyl group under the standard conditions [Pd(PPh3)4, Na2CO3, EtOH-H2O, reflux] yielded the target 3,4-diarylisoxazoles in good yields.