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11. 发明申请

WO2008115912A1 REGIO-SPECIFIC SYNTHESIS OF 4-BROMO-3-METHYL-5-PROPOXY-THIOPHENE-2-CARBOXYLIC ACID 审中-公开
标题翻译： 4-溴-3-甲基-5-丙氧基-2-羟基乙酸的特异性合成
公开(公告)号：WO2008115912A1
公开(公告)日：2008-09-25
申请号：PCT/US2008/057336
申请日：2008-03-18
申请人： SANOFI-AVENTIS , KUBIAK, Gregory G. , LYTHGOE, David J. , YU, Yong
发明人： KUBIAK, Gregory G. , LYTHGOE, David J. , YU, Yong
IPC分类号： C07D333/48
CPC分类号： C07D333/48
摘要： This invention is directed to a five step regio-specific synthesis of 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylic acid compound of formula 16 comprising the steps of acetalating 3-methyl-thiophene-2-carbaldehyde in an alcohol solvent; iodinating the acetalated 3-methyl-thiophene-2-carbaldehyde in an non-protic polar or hydrocarbon solvent to yield the corresponding iodinated and acetalated 3-methyl-thiophene-2-carbaldehyde product; treating the iodinated and acetalated product with water to yield the corresponding 5-iodo-3-methyl-thiophene-2-carbaldehyde; oxidizing the 5-iodo-3-methyl-thiophene-2-carbaldehyde to the corresponding 5-iodo-3-methyl-thiophene-2-carboxylic acid in ketone solvent; Ullmann coupling of the 5-iodo-3-methyl-thiophene-2-carboxylic acid with alkali metal propoxide salt using a copper catalyst in propanol to yield 3-methyl-5-propoxy-thiophene-2-carboxylic acid; esterifying 3-methyl-5-propoxy-thiophene-2-carboxylic acid to yield the corresponding alkyl 3-methyl-5-propoxy-thiophene-2-carboxylate; brominating the 3-methyl-5-propoxy-thiophene-2-carboxylic acid to yield the corresponding alkyl 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylate; and basic hydrolyzing the alkyl 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylate with base to yield 4-bromo-3-methyl-5-propoxy-thiophene-2-carboxylic acid.
摘要翻译：本发明涉及式16的4-溴-3-甲基-5-丙氧基 - 噻吩-2-羧酸化合物的五步区域特异性合成，包括以下步骤：将3-甲基 - 噻吩-2-甲醛缩醛醇溶剂; 在非质子极性或烃溶剂中碘化缩醛化的3-甲基 - 噻吩-2-甲醛，得到相应的碘化和缩醛化的3-甲基 - 噻吩-2-甲醛产物; 用水处理碘化和缩醛产物，得到相应的5-碘-3-甲基 - 噻吩-2-甲醛; 在酮溶剂中将5-碘-3-甲基 - 噻吩-2-甲醛氧化成相应的5-碘-3-甲基 - 噻吩-2-羧酸; 使用铜催化剂在丙醇中的5-碘-3-甲基 - 噻吩-2-羧酸与碱金属丙醇盐的Ullmann偶联，得到3-甲基-5-丙氧基 - 噻吩-2-羧酸; 酯化3-甲基-5-丙氧基 - 噻吩-2-羧酸，得到相应的3-甲基-5-丙氧基 - 噻吩-2-甲酸烷基酯; 溴化3-甲基-5-丙氧基 - 噻吩-2-羧酸，得到相应的4-溴-3-甲基-5-丙氧基 - 噻吩-2-羧酸烷基酯; 并用碱碱性水解4-溴-3-甲基-5-丙氧基 - 噻吩-2-羧酸烷基酯，得到4-溴-3-甲基-5-丙氧基 - 噻吩-2-羧酸。

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