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【结 构 式】

【分子编号】30763

【品名】[5-(methylsulfonyl)-1H-pyrrol-2-yl](phenyl)methanone

【CA登记号】

【 分 子 式 】C12H11NO3S

【 分 子 量 】249.29028

【元素组成】C 57.82% H 4.45% N 5.62% O 19.25% S 12.86%

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:(IX)

The benzoylation of 2-methylthiopyrrole (I) with N,N-dimethylbenzamide (II) by means of POCl3 in refluxing CH2Cl2 gives 5-benzoyl-2-methylthiopyrrole (III), which is condensed with spiro[2.5]-5,7-dioxa-6,6-dimethyloctane-4,8-dione (IV) by means of NaH in DMF yielding compound (V). The oxidation of (V) with m-chloroperbenzoic acid in CH2Cl2 affords the sulfone (VI), which is submitted to methanolysis with methanol and HCl giving 1-(3,3-dimethoxycarbonylpropyl)-2-methanesulfonyl-5-benzoylpyrrole (VII). The cyclization of (VII) with NaH in DMF yields dimethyl 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1,1-dicarboxylate (VIII), which is finally hydrolyzed and decarboxylated with KOH in refluxing methanol. Compound (III) can be oxidized with m-chloroperbenzoic acid as before giving 2-methanesulfonyl-5-benzoylpyrrole (IX), which is then condensed with spiro compound (IV) as before to afford compound (VI), already obtained.

1 Muchowski, J.M.; Franco, F.; Greenhouse, R.; Novel syntheses of 5-aryl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids. J Org Chem 1982, 47, 9, 1682-88.
2 Arrigoni-Martelli, E.; Castaner, J.; Blancafort, P.; Serradell, M.N.; RS-37,619. Drugs Fut 1983, 8, 10, 871.
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) 24831 2-(methylsulfanyl)-1H-pyrrole C5H7NS 详情 详情
(II) 30757 N,N-dimethylbenzamide 611-74-5 C9H11NO 详情 详情
(III) 30758 [5-(methylsulfanyl)-1H-pyrrol-2-yl](phenyl)methanone C12H11NOS 详情 详情
(IV) 11639 6,6-Dimethyl-5,7-dioxaspiro[2.5]octane-4,8-dione 5617-70-9 C8H10O4 详情 详情
(V) 30759 5-[2-[2-benzoyl-5-(methylsulfanyl)-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione C20H21NO5S 详情 详情
(VI) 30760 5-[2-[2-benzoyl-5-(methylsulfonyl)-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4,6-dione C20H21NO7S 详情 详情
(VII) 30761 dimethyl 2-[2-[2-benzoyl-5-(methylsulfonyl)-1H-pyrrol-1-yl]ethyl]malonate C19H21NO7S 详情 详情
(VIII) 30762 dimethyl 5-benzoyl-2,3-dihydro-1H-pyrrolizine-1,1-dicarboxylate C18H17NO5 详情 详情
(IX) 30763 [5-(methylsulfonyl)-1H-pyrrol-2-yl](phenyl)methanone C12H11NO3S 详情 详情
Extended Information