【结 构 式】 |
【分子编号】26233 【品名】2-butyl-7-methoxy-1-benzofuran-4-carboxylic acid 【CA登记号】 |
【 分 子 式 】C14H16O4 【 分 子 量 】248.27864 【元素组成】C 67.73% H 6.5% O 25.78% |
合成路线1
该中间体在本合成路线中的序号:(IV)Cyclization of bromophenol (I) with 1-hexyne (II) in the presence of Pd (0) and CuI catalysts produced benzofuran (III). Then, oxidation of the aldehyde function of (III) with sodium chlorite provided carboxylic acid (IV). An alternative route to the intermediate (IV) consisted of a palladium/copper-catalyzed cyclization of bromophenol (V) with 1-hexyne (II), followed by basic hydrolysis of the resulting benzofuran methyl ester (VI). Treatment of carboxylic acid (IV) with oxalyl chloride yielded the corresponding acid chloride (VII), which was finally condensed with 4-amino-3,5-dichloropyridine (VIII) in the presence of NaEt2AlH2 to furnish the target amide.
【1】 Hulme, C.; Travis, J.J.; Regan, J.R.; Djuric, S.W.; Sweeney, D.M.; Moriarty, K.J.; McGarry, D.G.; Miller, B.E.; Souness, J.E.; Volz, F.A.; Benzofuran based PDE4 inhibitors. Bioorg Med Chem 1999, 7, 6, 1131. |
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) | 26230 | 2-bromo-3-hydroxy-4-methoxybenzaldehyde | C8H7BrO3 | 详情 | 详情 | |
(II) | 26231 | 1-hexyne | 693-02-7 | C6H10 | 详情 | 详情 |
(III) | 26232 | 2-butyl-7-methoxy-1-benzofuran-4-carbaldehyde | C14H16O3 | 详情 | 详情 | |
(IV) | 26233 | 2-butyl-7-methoxy-1-benzofuran-4-carboxylic acid | C14H16O4 | 详情 | 详情 | |
(V) | 26234 | methyl 2-bromo-3-hydroxy-4-methoxybenzoate | C9H9BrO4 | 详情 | 详情 | |
(VI) | 26235 | methyl 2-butyl-7-methoxy-1-benzofuran-4-carboxylate | C15H18O4 | 详情 | 详情 | |
(VII) | 26236 | 2-butyl-7-methoxy-1-benzofuran-4-carbonyl chloride | C14H15ClO3 | 详情 | 详情 | |
(VIII) | 26135 | (2R,3R,4R)-4-(benzyloxy)-2-[(2,2-dimethylpropanoyl)oxy]-3-(formyloxy)-4-methyl-5-oxopentyl pivalate | C24H34O8 | 详情 | 详情 |