【结 构 式】 |
【分子编号】51316 【品名】2-Bromo-5-nitroanisole 【CA登记号】77337-82-7 |
【 分 子 式 】C7H6BrNO3 【 分 子 量 】232.03358 【元素组成】C 36.23% H 2.61% Br 34.44% N 6.04% O 20.69% |
合成路线1
该中间体在本合成路线中的序号:(I)The intermediate carbamate (V) has been obtained as follows. The reaction of 4-bromo-3-methoxynitrobenzene (I) with CuCN in NMP at 150 C gives 2-methoxy-4-nitrobenzonitrile (II), which is reduced with H2 over Pd/C in ethyl acetate to yield 4-amino-2-methoxybenzonitrile (III). Finally, this compound is condensed with phenyl carbamate (IV) by means of NaHCO3 in ethyl acetate to afford the desired carbamate intermediate (V).
【1】 Saunders, J.; Bethiel, S.; Badia, M.; Stamos, D.; Trudeau, M. (Vertex Pharmaceuticals Inc.); Inhibitors of IMPDH enzyme. WO 0056331 . |
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) | 51316 | 2-Bromo-5-nitroanisole | 77337-82-7 | C7H6BrNO3 | 详情 | 详情 |
(II) | 61931 | 2-methoxy-4-nitrobenzonitrile | C8H6N2O3 | 详情 | 详情 | |
(III) | 61932 | 4-amino-2-methoxybenzonitrile | C8H8N2O | 详情 | 详情 | |
(IV) | 33820 | phenyl carbamate | 622-46-8 | C7H7NO2 | 详情 | 详情 |
(V) | 61933 | phenyl 4-cyano-3-methoxyphenylcarbamate | C15H12N2O3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号:(II)Stille coupling between 2,5-bis(tri-n-butylstannyl)furan (I) and 2-bromo-5-nitroanisole (II) produced the 2,5-bis(4-nitrophenyl)furan (III), which was further reduced to the diamino derivative (IV) by catalytic hydrogenation over Pd/C. The title diamidine was then obtained by reaction of diamine (IV) with the S-(2-naphthylmethyl)thioimidate (V).
【1】 Stephens, C.E.; et al.; Diguanidino and " reversed" diamidino 2,5-diaryulfurans as antimicrobial agents. J Med Chem 2001, 44, 11, 1741. |
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) | 51315 | tributyl[5-(tributylstannyl)-2-furyl]stannane | C28H56OSn2 | 详情 | 详情 | |
(II) | 51316 | 2-Bromo-5-nitroanisole | 77337-82-7 | C7H6BrNO3 | 详情 | 详情 |
(III) | 51317 | 2-[5-(2-methoxy-4-nitrophenyl)-2-furyl]-5-nitrophenyl methyl ether; 2,5-bis(2-methoxy-4-nitrophenyl)furan | C18H14N2O7 | 详情 | 详情 | |
(IV) | 51318 | 4-[5-(4-amino-2-methoxyphenyl)-2-furyl]-3-methoxyphenylamine; 4-[5-(4-amino-2-methoxyphenyl)-2-furyl]-3-methoxyaniline | C18H18N2O3 | 详情 | 详情 | |
(V) | 51319 | 2-naphthylmethyl 2-pyridinecarbimidothioate | C17H14N2S | 详情 | 详情 |