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【结 构 式】

【分子编号】55753

【品名】6-(1H-imidazol-1-yl)-1-methyl-1H-indole

【CA登记号】

【 分 子 式 】C12H11N3

【 分 子 量 】197.23956

【元素组成】C 73.07% H 5.62% N 21.3%

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)

This compound has been obtained by two similar ways: The condensation of 6-iodo-1-methyl-1H-indole (I) with imidazole (II) by means of copper trifluoromethanesulfonate, 1,10-phenanthroline, Cs2CO3 and dibenzylideneacetone gives 6-(1-imidazolyl)-1-methyl-1H-indole (III), which is condensed with oxalyl chloride (IV) in dichloromethane to yield the adduct (V). Finally, this compound is cyclized with 2-(1-methyl-1H-indol-3-yl)acetimidic acid isopropyl ester (VI) by means of TEA in dichloromethane to afford the target pyrrolinedione. Alternatively, indole (I) and imidazole (II) are condensed by means of Pd2(dba)3, BINAP and tBu-ONa to give 6-(1-imidazolyl)-1-methyl-1H-indole (III), which is condensed with methoxalyl chloride (VII) in dichloromethane to yield the adduct (VIII). The reduction of (VIII) with NaH2PO2 affords the methyl acetate derivative (IX), which is treated with NH4OH to provide the acetamide derivative (X). Finally, this compound is cyclized with the methoxalyl derivative (XI) (obtained by condensation of 1-methyl-1H-indole (XII) with methoxalyl chloride (VII)) by means of tBu-ONa in THF to afford the target pyrrolinedione.

1 Kong, N.; Lovey, A.; Specian, A.; et al.; Design and synthesis of novel orally bioavailable, water soluble bisindolylmaleimides as cell cycle inhibitors. Proc Am Assoc Cancer Res 2002, 43.
2 Lovey, A.J.; Fotouhi, N.; Kong, N. (F. Hoffmann-La Roche AG); Substd. pyrroles. WO 0146178 .
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) 55752 6-iodo-1-methyl-1H-indole C9H8IN 详情 详情
(II) 10255 Imidazole; 1H-Imidazole 288-32-4 C3H4N2 详情 详情
(III) 55753 6-(1H-imidazol-1-yl)-1-methyl-1H-indole C12H11N3 详情 详情
(IV) 29841 Oxalyl chloride; 2-Chloro-2-oxoacetyl chloride 79-37-8 C2Cl2O2 详情 详情
(V) 55754 2-[6-(1H-imidazol-1-yl)-1-methyl-1H-indol-3-yl]-2-oxoacetyl chloride C14H10ClN3O2 详情 详情
(VI) 55755 isopropyl 2-(1-methyl-1H-indol-3-yl)ethanimidoate C14H18N2O 详情 详情
(VII) 26971 2-methoxy-2-oxoacetyl chloride 5781-53-3 C3H3ClO3 详情 详情
(VIII) 55756 methyl 2-[6-(1H-imidazol-1-yl)-1-methyl-1H-indol-3-yl]-2-oxoacetate C15H13N3O3 详情 详情
(IX) 55757 methyl 2-[6-(1H-imidazol-1-yl)-1-methyl-1H-indol-3-yl]acetate C15H15N3O2 详情 详情
(X) 55758 2-[6-(1H-imidazol-1-yl)-1-methyl-1H-indol-3-yl]acetamide C14H14N4O 详情 详情
(XI) 55759 methyl 2-(1-methyl-1H-indol-3-yl)-2-oxoacetate C12H11NO3 详情 详情
(XII) 14119 1-Methylindole; 1-Methyl-1H-indole 603-76-9 C9H9N 详情 详情
Extended Information