37928-17-9

Basic information

• Product Name: Isoxazole, 5-Methyl-3,4-diphenyl- (Parecoxib sodiuM inteMediate)
• Synonyms: Isoxazole, 5-Methyl-3,4-diphenyl- (Parecoxib sodiuM inteMediate);Isoxazole, 5-Methyl-3,4-diphenyl-;3,4-Diphenyl-5-methylisoxazole;5-Methyl-3,4-diphenylisoxazole;3-Phenyl-4-(4-aMinosulfonylbenzyl)-5-Methylisoxazole,Valdecoxib IMpurity A;Parecoxib SodiuM interMediate A;Parecoxib InterMediate (5-Mehyl-3,4-Diphenylisoxazole);5-Methyl-3,4-diphenyl- (Parecoxib sodiuM inteMediate)
• CAS NO: 37928-17-9
• Molecular Formula: C₁₆H₁₃NO
• Molecular Weight: 235.28052
• EINECS: 1592732-453-0
• Product Categories: API
• Mol File: 37928-17-9.mol
• Article Data: 27

Chemical Properties

• Melting Point: 96.0 to 100.0 °C
• Boiling Point: 340.1±21.0 °C(Predicted)
• Appearance: /
• Density: 1.108±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• PKA: -2.53±0.50(Predicted)
• CAS DataBase Reference: Isoxazole, 5-Methyl-3,4-diphenyl- (Parecoxib sodiuM inteMediate)(CAS DataBase Reference)
• NIST Chemistry Reference: Isoxazole, 5-Methyl-3,4-diphenyl- (Parecoxib sodiuM inteMediate)(37928-17-9)
• EPA Substance Registry System: Isoxazole, 5-Methyl-3,4-diphenyl- (Parecoxib sodiuM inteMediate)(37928-17-9)

Safety Data

• Hazardous Substances Data: 37928-17-9(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 37928-17-9 differently. You can refer to the following data:
1. 5-Methyl-3,4-diphenylisoxazole is synthesis The key intermediate of Parecoxib Sodium (Parecoxib Sodium).Parecoxib Sodium is by the Pfizer of the U.S. The cox 2 inhibitor of company's research and development, listed in European Union in 2002, trade name Dynastat, is used for The short term therapy of postoperative pain.
2. 5-Methyl-3,4-diphenylisoxazole is a reagent for the preparation of valdecoxib and valdecoxib analogues.

Synthesis

In four mouthfuls of round-bottomed flasks of a 1L add compound 2 (40g), methanol (400mL), 7.7% Aqueous sodium carbonate (400mL), is heated to 70 DEG C, after stirring reaction 2h, and TLC plate monitoring raw material Fundamental reaction is complete, and solution is divided into solid-liquid biphase, is extracted with ethyl acetate, collected organic layer, with anhydrous Sodium sulfate is dried, and vacuum obtains white solid, HPLC purity: 94.9% after being spin-dried for.White solid uses 40ml ethyl acetate and the mixed solvent recrystallization of 120ml normal hexane (1:3) again, Obtaining target compound is white solid 34.2g, yield 92%, HPLC purity: 99.7%.m.p.97-98℃； MS(m/z):236(M+H)+；1H NMR(400MHz,CDCl3) δ:2.43(s,3H,-CH3), 7.19-7.43 (m, 10H ,-CH=).

Upstream product

• 42353-58-2 1-(1,2-diphenyl-vinyl)-pyrrolidine 
• 873-67-6 benzonitrile oxide 
• 52201-28-2 1-(1-methyl-2-phenyl ethenyl)-pyrrolidine 
• 26306-06-9 (E)-benzyl phenyl ketoxime 
• 64-19-7 acetic acid 
• 5455-12-9 1,3-diphenyl-but-2-en-1-one oxime 
• 80954-52-5 N,N-diethyl-2,3-dihydro-2-methyl-3,4-diphenyl-2-azetecarboxamide 1-oxide 
• 181696-73-1 3,4-diphenyl-4-hydrido-5-hydroxy-5-methylisoxazole 
• 83152-72-1 (Z)-N,N-diethyl-4-(hydroxyimino)-2-methyl-3,4-diphenyl-2-butenamide 
• 75115-03-6 4-Bromo-5-methyl-3,5-diphenyl-4,5-dihydro-isoxazole 
• 857259-65-5 5-methyl-3,4-diphenyl-5-(pyrrolidin-1-yl)-4,5-dihydroisoxazole 
• 1403477-84-8 1,2-diphenyl-but-3-en-1-one oxime 
• 89703-88-8 2-phenyl-1-phenyl-3-buten-1-one 
• 84363-90-6 1,2-diphenylbut-3-en-1-ol 

Downstream Products

• 1373038-57-3 C₁₆H₁₂ClNO₃S 
• 509074-26-4 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonyl chloride 
• 1373038-56-2 3-(5-methyl-4-phenylisoxazol-3-yl)benzenesulfonamide 
• 181695-72-7 valdecoxib 
• 1373038-63-1 C₁₆H₁₁Cl₂NO₅S₂ 
• 1373038-59-5 C₁₆H₁₅N₃O₅S₂ 
• 1373038-60-8 C₃₂H₂₅N₃O₆S₂ 
• 198470-84-7 parecoxib 
• 386273-25-2 [3-(5-methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonamide 
• 1709956-95-5 [3-(5-methyl-3-phenyl-4-isoxazolyl)phenyl]sulfonyl chloride 
• 1037546-03-4 2-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonyl chloride 
• 181695-75-0 4-[3-(3-fluoro-4-methoxyphenyl)-5-methyl-isoxazol-4-yl]benzenesulfonamide 
• 181696-35-5 5-methyl-3-phenyl-4-(4-sulfophenyl)isoxazole 

Relevant articles and documents

NHC-palladium-catalyzed ionic liquid-accelerated regioselective oxyarylation of alkynes with diaryl ethers?

The first NHC-palladium-catalyzed regioselective oxyarylation of oxime ether in a task-specific ionic liquid via C(sp3)-O and C(sp2)-O bond cleavage of two different types of ethers for the assembly of structurally diverse 4-arylisoxazoles is described. Both the basic ionic liquid [C3NH2mim]Br and NHC-Pd catalyst IPr-Pd-Im-Cl2 played an important role in this transformation. Notably, this new approach provides a practical and straightforward route to access a broad range of privileged 4-arylisoxazole structures with good yields and excellent regioselectivities. Significantly, this catalytic system can be recycled up to eight times without significant loss of catalytic activity.

Method for preparing parecoxib sodium key intermediates

The invention relates to a method for preparing parecoxib sodium key intermediates, and belongs to the field of medicine synthesis. The method for preparing the parecoxib sodium key intermediates includes steps of firstly, preparing 1-(1-methyl-2-styrene)-pyrrolidine (a compound I); secondly, preparing 5-methyl-3, 4-diphenyl-5-(pyrrolidine-1-base)-4, 5-dihydro-isoxazole (a compound II); thirdly, preparing a crude product of 5-methyl-3, 4-diphenyl isoxazole (a compound III); fourthly, refining a crude product of 5-methyl-3, 4-diphenyl-5-isoxazole (a compound III). The shortcomings of existing synthesis methods can be overcome by the aid of the method. The method for preparing the parecoxib sodium key intermediates has the advantages of mild reaction conditions, inexpensive and easily available raw materials, simplicity in after-treatment operation, short production cycle and high product purity and yield. Besides, the novel method is provided for preparing the parecoxib sodium key intermediates.

Method for preparing parecoxib intermediate

The invention discloses a method for preparing a parecoxib intermediate. The method includes subjecting 1, 2-diphenyl-2-acetyl ethyl ketone and ammonium acetate to contact reaction with the presence of iodobenzene diacetate and potassium iodide, performing organic-phase concentration and washing after reaction, performing ethyl alcohol recrystallization, and drying to obtain 5-methyl-3, 4-diphenyl isoxazole. The method for preparing the parecoxib intermediate has the advantages of simplicity in procedure and high yield.