DIBRT
Chemical Name: 3,5-Dibromo-4-(4-hydroxy-3,5-diisopropylphenoxy)benzoic acid
CAS No. 192766-84-0
项目整合开发状态: Biological Testing
项目研究机构: Karo Bio (Originator), University of California, San Francisco (Originator)
合成路线:By reaction of 4-nitro-4?aminodiphenylamine (I) with N,N-diethylthiocarbamoyl chloride (II),ammonium thiocyanate (III),thiophosgene (IV),or bis-(N,N-diethylthiocarbamoyl)disulfide (V) in the appropriate solvent
合成路线:Methylation of 2,6-diisopropylphenol (I) with iodomethane and K2CO3 provides ether (II).Subsequent treatment with iodine and nitric acid gives rise to the diaryl iodonium compound (III),isolated as the corresponding tetrafluoroborate salt.3,5-Dibromo-4-hydroxybenzoic acid (IV) is esterified with methanol and thionyl chloride to produce (V).Copper-promoted coupling between hydroxybenzoate (V) and the diaryl iodonium salt (III) leads to diaryl ether (VI).Finally,simultaneous cleavage of the methyl ether and ester groups of (VI) is achieved by means of boron tribromide in cold CH2Cl2
📌 参考资料/链接：
参考文献标题:Nuclear receptor ligands and ligand binding domains
文献作者:Brenneisen,P.; et al.(Ciba Geigy Corp.)
参考来源:DE 1932690; DE 1935338; US 3839582
📄 详细内容
合成路线:Methylation of 2,6-diisopropylphenol (I) with iodomethane and K2CO3 provides ether (II).Subsequent treatment with iodine and nitric acid gives rise to the diaryl iodonium compound (III),isolated as the corresponding tetrafluoroborate salt.3,5-Dibromo-4-hydroxybenzoic acid (IV) is esterified with methanol and thionyl chloride to produce (V).Copper-promoted coupling between hydroxybenzoate (V) and the diaryl iodonium salt (III) leads to diaryl ether (VI).Finally,simultaneous cleavage of the methyl ether and ester groups of (VI) is achieved by means of boron tribromide in cold CH2Cl2
参考文献标题:Nuclear receptor ligands and ligand binding domains
文献作者:Baxter,J.D.; Scanlan,T.S.; Fletterick,R.J.; Wagner,R.L.; Kushner,P.J.; West,B.L.; Shiau,A.K.; Apriletti,J.W.(University of California,Oakland)
参考来源:CA 2314096; EP 1034184; US 6266622; WO 9926966
合成路线:Methylation of 2,6-diisopropylphenol (I) with iodomethane and K2CO3 provides ether (II).Subsequent treatment with iodine and nitric acid gives rise to the diaryl iodonium compound (III),isolated as the corresponding tetrafluoroborate salt.3,5-Dibromo-4-hydroxybenzoic acid (IV) is esterified with methanol and thionyl chloride to produce (V).Copper-promoted coupling between hydroxybenzoate (V) and the diaryl iodonium salt (III) leads to diaryl ether (VI).Finally,simultaneous cleavage of the methyl ether and ester groups of (VI) is achieved by means of boron tribromide in cold CH2Cl2
参考文献标题:Structure-based design and synthesis of a thyroid hormone receptor (TR) antagonist
文献作者:Baxter,J.D.; Goede,P.; Apriletti,J.W.; West,B.L.; Feng,W.; Mellstrom,K.; Fletterick,R.J.; Wagner,R.L.; Kushner,P.J.; Ribeiro,R.C.; Webb,P.; Scanlan,T.S.; Nilsson,S.
参考来源:Endocrinology 2002,143(2),517