methyl 3,5-dibromo-4-(3,5-diisopropyl-4-methoxyphenoxy)benzoate -Drug Synthesis Database

【结构式】

【分子编号】60876

【品名】methyl 3,5-dibromo-4-(3,5-diisopropyl-4-methoxyphenoxy)benzoate

【CA登记号】

【分子式】C₂₁H₂₄Br₂O₄

【分子量】500.22716

【元素组成】C 50.42% H 4.84% Br 31.95% O 12.79%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(VI)

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

参考文献中间体

合成目标

【1】 Baxter, J.D.; Goede, P.; Apriletti, J.W.; et al.; Structure-based design and synthesis of a thyroid hormone receptor (TR) antagonist. Endocrinology 2002, 143, 2, 517.
【2】 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); Nuclear receptor ligands and ligand binding domains. CA 2314096; EP 1034184; US 6266622; WO 9926966 .
【3】 Brenneisen,P.; et al. (Ciba Geigy Corp.); Nuclear receptor ligands and ligand binding domains. DE 1932690; DE 1935338; US 3839582 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	20249	2,6-Diisopropylphenol	2078-54-8	C₁₂H₁₈O	详情	详情
(II)	60874	2,6-diisopropylphenyl methyl ether; 1,3-diisopropyl-2-methoxybenzene		C₁₃H₂₀O	详情	详情
(III)	60875	bis(3,5-diisopropyl-4-methoxyphenyl)iodonium		C₂₆H₃₈IO₂	详情	详情
(IV)	10115	3,5-Dibromo-4-hydroxybenzoic acid	3337-62-0	C₇H₄Br₂O₃	详情	详情
(V)	10116	methyl 3,5-dibromo-4-hydroxybenzoate	41727-47-3	C₈H₆Br₂O₃	详情	详情
(VI)	60876	methyl 3,5-dibromo-4-(3,5-diisopropyl-4-methoxyphenoxy)benzoate		C₂₁H₂₄Br₂O₄	详情	详情

Extended Information