1139901-88-4

Basic information

• Product Name: tert-butyl 2-(3’-cyano-4’-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• Synonyms: tert-butyl 2-(3’-cyano-4’-isobutoxyphenyl)-4-methylthiazole-5-carboxylate
• CAS NO: 1139901-88-4
• Molecular Weight: 372.488
• Mol File: 1139901-88-4.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: tert-butyl 2-(3’-cyano-4’-isobutoxyphenyl)-4-methylthiazole-5-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: tert-butyl 2-(3’-cyano-4’-isobutoxyphenyl)-4-methylthiazole-5-carboxylate(1139901-88-4)
• EPA Substance Registry System: tert-butyl 2-(3’-cyano-4’-isobutoxyphenyl)-4-methylthiazole-5-carboxylate(1139901-88-4)

Safety Data

• Hazardous Substances Data: 1139901-88-4(Hazardous Substances Data)

Upstream product

• 905857-41-2 tert-butyl 4-methylthiazole-5-carboxylate 
• 1139901-87-3 5-iodo-2-isobutoxy-benzonitrile 
• 179897-89-3 5-Bromo-2-fluoro-benzonitrile 
• 20485-41-0 4-methylthiazole-5-carboxylic acid 
• 351003-36-6 2-fluoro-5-iodobenzonitrile 
• 876918-26-2 5-bromo-2-isobutoxy-benzonitrile 
• 144649-99-0 5-bromo-2-methoxybenzonitrile 
• 40530-18-5 5-bromo-2-hydroxybenzonitrile 
• 14804-31-0 2-methyl-4-bromoanisole 
• 184970-28-3 4-bromo-2-(bromomethyl)-1-methoxybenzene 
• 30752-23-9 4-bromophenyl iso-butyl ether 
• 1304385-08-7 4-iodophenyl isobutyl ether 
• 106-41-2 4-bromo-phenol 
• 540-38-5 p-Iodophenol 

Downstream Products

• 144060-53-7 febuxostat 

Relevant articles and documents

Process Development of Febuxostat Using Palladium- and Copper-Catalyzed C-H Arylation

There is significant interest in the development of process routes for active pharmaceutical ingredients using C-H arylation methodology. An efficient and practical synthetic route for febuxostat (1), which is the first non-purine-type xanthine oxidase inhibitor, was established via palladium- and copper-catalyzed C-H arylation of thiazole with aryl bromide. The catalyst loading was reduced to 0.1 mol percent for the intermolecular C-H arylation, and a three-step synthesis produced febuxostat in 89percent overall yield with excellent selectivity.

Facile one-pot transformation of arenes into aromatic nitriles under metal-cyanide-free conditions

Electron-rich arenes bearing methyl or methoxy groups on the aromatic ring were treated with dichloromethyl methyl ether and ZnBr2, and then with molecular iodine and aq. ammonia to give the corresponding aromatic nitriles in good yields. Using this method, febuxostat was efficiently prepared from 4-bromophenol in four steps. The method can be used for the preparation of aromatic nitriles from arenes in one pot under metal-cyanide-free conditions. Various electron-rich arenes could be effectively converted into the corresponding aromatic nitriles in good yields, by treatment with ZnBr2 and dichloromethyl methyl ether, followed by reaction with molecular iodine and aq. ammonia.

Direct oxidative conversion of methylarenes into aromatic nitriles

A variety of methylarenes were successfully converted into the corresponding aromatic nitriles in good to moderate yields by the treatment with NBS or DBDMH in the presence of a catalytic amount of AIBN or BPO, followed by the reaction with molecular iodine in aq NH3 in a one-pot procedure. The present reaction is a useful and practical transition-metal-free method for the preparation of aromatic nitriles from methylarenes.