ethyl 2-{2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenoxy}acetate -Drug Synthesis Database

【结构式】

【分子编号】56244

【品名】ethyl 2-{2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenoxy}acetate

【CA登记号】

【分子式】C₂₀H₁₈I₂O₄

【分子量】576.16946

【元素组成】C 41.69% H 3.15% I 44.05% O 11.11%

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：(VIII)

Friedel-Crafts acylation of 2-methylbenzofuran (I) with p-anisoyl chloride (II) in the presence of SnCl4 afforded the benzoyl benzofuran derivative (III). Ketone (III) reduction to the corresponding benzyl benzofuran (IV) was accomplished employing either LiAlH4 or NaBH4 and ZnI2. The methyl ether group of (IV) was then cleaved with melted pyridine hydrochloride to give phenol (V). Aromatic iodination of (V) with either I2/KI or with ICl in morpholine led to the diiodo phenol (VI). This was then alkylated with ethyl bromoacetate (VII) to furnish ester (VIII), which was finally hydrolyzed with NaOH to the target carboxylic acid.

参考文献中间体

合成目标

【1】 Singh, B.N.; Malm, J.; Mellin, C.; Li, Y.-L.; Nilsson, S.; Temciuc, M.; Carlsson, B.; Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone. J Med Chem 2002, 45, 3, 623.
【2】 Norinder, U.; Bajorath, J.; Stearns, J.F. (Karo Bio AB); Receptor ligands. WO 9220331 .

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)	56239	2-Methylbenzofuran		C₉H₈O	详情	详情
(II)	22671	4-Methoxybenzoyl chloride; p-Methoxybenzoyl chloride; 4-Anisoyl chloride	100-07-2	C₈H₇ClO₂	详情	详情
(III)	56240	(4-methoxyphenyl)(2-methyl-1-benzofuran-3-yl)methanone		C₁₇H₁₄O₃	详情	详情
(IV)	56241	3-(4-methoxybenzyl)-2-methyl-1-benzofuran; methyl 4-[(2-methyl-1-benzofuran-3-yl)methyl]phenyl ether		C₁₇H₁₆O₂	详情	详情
(V)	56242	4-[(2-methyl-1-benzofuran-3-yl)methyl]phenol		C₁₆H₁₄O₂	详情	详情
(VI)	56243	2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenol		C₁₆H₁₂I₂O₂	详情	详情
(VII)	16640	Ethyl 2-bromoacetate; Ethyl bromoacetate	105-36-2	C₄H₇BrO₂	详情	详情
(VIII)	56244	ethyl 2-{2,6-diiodo-4-[(2-methyl-1-benzofuran-3-yl)methyl]phenoxy}acetate		C₂₀H₁₈I₂O₄	详情	详情

Extended Information