2-butyl-7-methoxy-1-benzofuran-4-carbaldehyde -Drug Synthesis Database

【结构式】

【分子编号】26232

【品名】2-butyl-7-methoxy-1-benzofuran-4-carbaldehyde

【CA登记号】

【分子式】C₁₄H₁₆O₃

【分子量】232.27924

【元素组成】C 72.39% H 6.94% O 20.66%

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：(III)

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.

参考文献中间体

合成目标

【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

Extended Information