3-(2-iodoanilino)-2-cyclohexen-1-one -Drug Synthesis Database

【结构式】

【分子编号】53899

【品名】3-(2-iodoanilino)-2-cyclohexen-1-one

【CA登记号】n/a

【分子式】C₁₂H₁₂INO

【分子量】313.13789

【元素组成】C 46.03% H 3.86% I 40.53% N 4.47% O 5.11%

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)

Condensation of 2-iodoaniline (I) with cyclohexane-1,3-dione (II) at 120 C yields secondary amine (III), which is then methylated with iodomethane by means of sodium hydride in refluxing benzene to provide tertiary amine (IV). Treatment of (IV) with lithium diisopropylamide (LDA) and dimethylaminomethylene iodide (Eschenmoser's salt) (V) in THF yields dimethylaminomethyl derivative (VI), which is then coupled with 2-methylindole (VII) in DMF to give compound (VIII). Cyclization of cyclohexenone derivative (VIII) by means of palladium (II) acetate and triethylamine in acetonitrile provides carbazolone derivative (IX), which is finally converted into the desired hydrochloride salt by treatment with HCl.

参考文献中间体

合成目标

【1】 Bell, J.A.; Ewan, G.B.; Humber, D.C.; Costes, I.H.; Godfrey, N. (GlaxoSmithKline plc); Process for the preparation of 3-imidazolylmethyltetrahydrocarbazolones. EP 0221629 .

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)	27725	2-iodoaniline	615-43-0	C₆H₆IN	详情	详情
(II)	11244	1,3-Cyclohexanedione	504-02-9	C₆H₈O₂	详情	详情
(III)	53899	3-(2-iodoanilino)-2-cyclohexen-1-one	n/a	C₁₂H₁₂INO	详情	详情
(IV)	53900	3-[2-iodo(methyl)anilino]-2-cyclohexen-1-one	n/a	C₁₃H₁₄INO	详情	详情
(V)	48555	Eschenmoser's salt; N,N-Dimethylmethyleneimmonium chloride; N,N-Dimethylmethyleneimmonium iodide		C₃H₈IN	详情	详情
(VI)	53901	6-[(dimethylamino)methyl]-3-[2-iodo(methyl)anilino]-2-cyclohexen-1-one	n/a	C₁₆H₂₁IN₂O	详情	详情
(VII)	15670	2-Methylimidazole; 2-Methyl-1H-imidazole	693-98-1	C₄H₆N₂	详情	详情
(VIII)	53902	3-[2-iodo(methyl)anilino]-6-[(2-methyl-1H-imidazol-1-yl)methyl]-2-cyclohexen-1-one	n/a	C₁₈H₂₀IN₃O	详情	详情
(IX)	53903	9-methyl-3-[(2-methyl-1H-imidazol-1-yl)methyl]-1,2,3,9-tetrahydro-4H-carbazol-4-one	n/a	C₁₈H₁₉N₃O	详情	详情

Extended Information