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【结 构 式】 
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【分子编号】38848 【品名】3-(chloromethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione 【CA登记号】 |
【 分 子 式 】C12H12ClNO3 【 分 子 量 】253.68492 【元素组成】C 56.82% H 4.77% Cl 13.98% N 5.52% O 18.92% |
合成路线1
该中间体在本合成路线中的序号：(VIII)Alkylation of 5-methoxy-2-methylindole (I) with iodomethane and NaH afforded the 1,2-dimethyl derivative (II). Subsequent Vilsmeier formylation of (II) employing N-methylformanilide and POCl3 furnished aldehyde (III). Nitration of (III) to (IV), followed by reduction with Sn and HCl gave aminoindole (V), which was oxidized to the corresponding quinone (VI) by using a buffered solution of Fremy's salt. Aldehyde (VI) reduction with NaBH4 provided alcohol (VII). This was optionally converted to the chloromethyl derivative (VIII) upon treatment with SOCl2. The title p-nitrophenyl ether was either obtained by alkylation of 4-nitrophenol (IX) with chloride (VIII) or by Mitsunobu coupling of 4-nitrophenol (IX) with indole alcohol (VII).
| 【1】 Beall, H.D.; Winski, S.; Swann, E.; Hudnott, A.R.; Cotterill, A.S.; O'Sullivan, N.; Green, S.J.; Bien, R.; Siegel, D.; Ross, D.; Moody, C.J.; Indolequinone antitumor agents: Correlation between quinone structure, rate of metabolism by recombinant human NAD(P)H:quinone oxidoreductase, and in vitro cytotoxicity. J Med Chem 1998, 41, 24, 4755. |
| 【2】 Stratford, I.J.; Naylor, M.A.; Jaffar, M.; Adams, G.E. (BTG plc); Indoloquinone derivs. as bioreductive agents. WO 9723456 . |
| 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) | 38842 | 5-Methoxy-2-methyl-1H-indole; Methyl 2-methyl-1H-indol-5-yl ether | 1076-74-0 | C10H11NO | 详情 | 详情 |
| (II) | 38843 | 1,2-dimethyl-1H-indol-5-yl methyl ether; 5-methoxy-1,2-dimethyl-1H-indole | C11H13NO | 详情 | 详情 | |
| (III) | 38844 | 5-methoxy-1,2-dimethyl-1H-indole-3-carbaldehyde | C12H13NO2 | 详情 | 详情 | |
| (IV) | 38845 | 5-methoxy-1,2-dimethyl-4-nitro-1H-indole-3-carbaldehyde | C12H12N2O4 | 详情 | 详情 | |
| (V) | 38846 | 4-amino-5-methoxy-1,2-dimethyl-1H-indole-3-carbaldehyde | C12H14N2O2 | 详情 | 详情 | |
| (VI) | 38847 | 5-methoxy-1,2-dimethyl-4,7-dioxo-4,7-dihydro-1H-indole-3-carbaldehyde | C12H11NO4 | 详情 | 详情 | |
| (VII) | 26107 | 3-(hydroxymethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione | C12H13NO4 | 详情 | 详情 | |
| (VIII) | 38848 | 3-(chloromethyl)-5-methoxy-1,2-dimethyl-1H-indole-4,7-dione | C12H12ClNO3 | 详情 | 详情 | |
| (IX) | 11236 | 4-Nitrophenol; p-Nitrophenol | 100-02-7 | C6H5NO3 | 详情 | 详情 |