【结 构 式】 |
【分子编号】50822 【品名】(2-hydroxy-5-nitrobenzyl)(triphenyl)phosphonium bromide 【CA登记号】 |
【 分 子 式 】C25H21BrNO3P 【 分 子 量 】494.324442 【元素组成】C 60.74% H 4.28% Br 16.16% N 2.83% O 9.71% P 6.27% |
合成路线1
该中间体在本合成路线中的序号:(II)Treatment of 2-hydroxy-5-nitrobenzyl bromide (I) with triphenylphosphine in refluxing chloroform provides phosphonium bromide derivative (II), which is converted into 2-butyl-5-nitro benzofuran (IV) by first reaction with pentanoyl chloride (III) in refluxing chloroform in the presence of pyridine, followed by treatment with Et3N in refluxing toluene. Acylation of (IV) with anisoyl chloride (V) by means of tin tetrachloride in dichloroethane furnishes 2-butyl-3-(4-methoxy benzoyl)-5-nitro benzofuran (VI), whose methoxy group is then converted into an hydroxy group by treatment with aluminum chloride in refluxing dichloroethane, yielding hydroxy benzoyl derivative (VII). Condensation of (VII) with N,N-dibutyl-N-(3-chloropropyl)amine (VIII) by means of K2CO3 in refluxing butanone affords compound (IX), which is then hydrogenated over PtO2 in EtOH to give amino derivative (X). Finally, the target product is obtained by reaction of (X) with methanesulfonyl chloride and Et3N in dichloroethane and hydrochloride salt formation with HCl in AcOEt/ethyl ether.
【1】 Gubin, J.; Lucchetti, J.; Inion, H.; Chatelain, P.; Rosseels, G.; Kilenyi, S. (Sanofi-Synthélabo); Benzofuran derivs., benzothiophenes, indoles or indolizines, process for production and compsns. containing them. EP 0471609; FR 2665444; JP 1992316554; US 5223510 . |
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) | 50821 | alpha-Bromo-4-nitro-o-cresol; Koshland's reagent; 2-Hydroxy-5-nitrobenzyl bromide | 772-33-8 | C7H6BrNO3 | 详情 | 详情 |
(II) | 50822 | (2-hydroxy-5-nitrobenzyl)(triphenyl)phosphonium bromide | C25H21BrNO3P | 详情 | 详情 | |
(III) | 15116 | pentanoyl chloride; valeryl chloride | 638-29-9 | C5H9ClO | 详情 | 详情 |
(IV) | 50823 | 2-butyl-5-nitro-1-benzofuran | C12H13NO3 | 详情 | 详情 | |
(V) | 22671 | 4-Methoxybenzoyl chloride; p-Methoxybenzoyl chloride; 4-Anisoyl chloride | 100-07-2 | C8H7ClO2 | 详情 | 详情 |
(VI) | 50824 | (2-butyl-5-nitro-1-benzofuran-3-yl)(4-methoxyphenyl)methanone | C20H19NO5 | 详情 | 详情 | |
(VII) | 50825 | (2-butyl-5-nitro-1-benzofuran-3-yl)(4-hydroxyphenyl)methanone | C19H17NO5 | 详情 | 详情 | |
(VIII) | 50826 | N,N-dibutyl-N-(3-chloropropyl)amine; N-butyl-N-(3-chloropropyl)-1-butanamine | 36421-15-5 | C11H24ClN | 详情 | 详情 |
(IX) | 50827 | (2-butyl-5-nitro-1-benzofuran-3-yl)[4-[3-(dibutylamino)propoxy]phenyl]methanone | C30H40N2O5 | 详情 | 详情 | |
(X) | 50828 | (5-amino-2-butyl-1-benzofuran-3-yl)[4-[3-(dibutylamino)propoxy]phenyl]methanone | C30H42N2O3 | 详情 | 详情 |