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【结 构 式】

【分子编号】39562

【品名】7-bromo-1,3-benzodioxole-5-carbaldehyde

【CA登记号】

【 分 子 式 】C8H5BrO3

【 分 子 量 】229.0299

【元素组成】C 41.95% H 2.2% Br 34.89% O 20.96%

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:(XI)

The starting phenylethylamine (I) is prepared by condensation of N-formyl-5-bromo-3,4-methylenedioxyphenylethylamine (VIII) with N-carbobenzoxy-3-methoxy-4-hydroxyphenylethylamine (IX) through an Ullman condensation catalysed by CuO, followed by elimination of the formyl group with HCl in methanol. Compound (VIII) is prepared as follows: 3,4-dihydroxy-5-bromobenzaldehyde (X) is methylenated with methylene bromide (A) and CuO in DMF giving 3,4-methylenedioxy-5-bromobenzaldehyde (XI), which is condensed with nitromethane (B) in acetic acid containing ammonium acetate affording 3,4-methylenedioxy-5-bromo-beta-nitrostyrene (XII). The reduction of (XII) under Clemensen conditions yields 3,4-methylenedioxy-5-bromophenylethylamine (XIII), which is finally formylated with formic acid in decalin. Compound (IX) is prepared as follows: 3-methoxy-4-hydroxy-beta-nitrostyrene (XIV) is treated with ethyl chloroformate (C) in pyridine yielding the corresponding ethoxycarbonyl derivative (XV), which is reduced under Clemensen conditions to 3-methoxy-4-ethoxycarbonyloxyphenylethylamine (XVI). Finally, this compound is treated first with benzyloxycarbonyl chloride and then with aqueous NaHCO3.

1 Tomita, M.; et al.; Synthesis of di-cepharanthine. Tetrahedron Lett 1967, 1201-06.
2 Serradell, M.N.; Blancafort, P.; Mealy, N.; Castañer, J.; Cepharanthine. Drugs Fut 1979, 4, 7, 481.
3 Kondo, H.; et al.; US 2206407 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 10252 1,2-Dibromoethane; Ethylene dibromide 106-93-4 C2H4Br2 详情 详情
(B) 39563 nitromethane 75-52-5 CH3NO2 详情 详情
(I) 39554 benzyl 4-[[6-(2-aminoethyl)-1,3-benzodioxol-4-yl]oxy]-3-methoxyphenethylcarbamate C26H28N2O6 详情 详情
(VIII) 39566 2-(7-bromo-1,3-benzodioxol-5-yl)ethylformamide C10H10BrNO3 详情 详情
(IX) 39570 benzyl 3-hydroxy-4-methoxyphenethylcarbamate C17H19NO4 详情 详情
(X) 39561 3-bromo-4,5-dihydroxybenzaldehyde 16414-34-9 C7H5BrO3 详情 详情
(XI) 39562 7-bromo-1,3-benzodioxole-5-carbaldehyde C8H5BrO3 详情 详情
(XII) 39564 4-bromo-6-[(E)-2-nitroethenyl]-1,3-benzodioxole C9H6BrNO4 详情 详情
(XIII) 39565 2-(7-bromo-1,3-benzodioxol-5-yl)ethylamine; 2-(7-bromo-1,3-benzodioxol-5-yl)-1-ethanamine C9H10BrNO2 详情 详情
(XIV) 39567 2-methoxy-5-[(E)-2-nitroethenyl]phenol C9H9NO4 详情 详情
(XV) 39568 ethyl 2-methoxy-5-[(E)-2-nitroethenyl]phenyl carbonate C12H13NO6 详情 详情
(XVI) 39569 5-(2-aminoethyl)-2-methoxyphenyl ethyl carbonate C12H17NO4 详情 详情
(C) 11229 1-[(Chlorocarbonyl)oxy]ethane;ethyl carbonochloridate; Carbonchloridic acid ethyl ester;Ethyl chloroformate;Ethyl chlorocarbonate 541-41-3 C3H5ClO2 详情 详情
Extended Information