【结 构 式】 |
【分子编号】53901 【品名】6-[(dimethylamino)methyl]-3-[2-iodo(methyl)anilino]-2-cyclohexen-1-one 【CA登记号】n/a |
【 分 子 式 】C16H21IN2O 【 分 子 量 】384.26009 【元素组成】C 50.01% H 5.51% I 33.03% N 7.29% O 4.16% |
合成路线1
该中间体在本合成路线中的序号:(VI)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.
【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 |