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【结 构 式】

【分子编号】57604

【品名】6-bromo-5-methyl-2-pyridinecarbonitrile

【CA登记号】

【 分 子 式 】C7H5BrN2

【 分 子 量 】197.03418

【元素组成】C 42.67% H 2.56% Br 40.55% N 14.22%

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:(III)

2-Bromo-3-methylpyridine (I) is converted to the corresponding N-oxide (II) by treatment with m-chloroperbenzoic acid in CH2Cl2. Reaction of N-oxide (II) with trimethylsilyl cyanide and dimethylcarbamoyl chloride gives rise to the 2-cyanopyridine (III). Subsequent radical bromination of (III) using NBS and AIBN affords the bromomethyl pyridine (IV). Lithiation of 1-methyl-2-(triethylsilyl)imidazole (V), followed by condensation with 4-cyanobenzaldehyde (VI), provides carbinol (VII). This is then condensed with bromide (IV) in the presence of Ag2O to give ether (VIII). 5-Bromo-2,2-difluorobenzodioxole (IX) is lithiated with butyllithium in cold Et2O and subsequently treated with triisopropyl borate to afford, after aqueous work-up, the arylboronic acid (X). Finally, Mitsunobu coupling between boronic acid (X) and the bromopyridine (VIII) provides the title compound.

1 Wang, L.; Hasvold, L.; Tong, Y.; et al.; Discovery of potent and orally active farnesyltransferase inhibitors. 224th ACS Natl Meet (Aug 18 2002, Boston) 2002, Abst MEDI 129.
2 Sham, H.L.; Rockway, T.W.; Li, T.; Mantei, R.A.; Li, Q.; Lin, N.-H.; Wang, L.; Wang, W.; Wang, X.; Sullivan, G.M.; Wang, G.T.; Gwaltney, S.L. II; Claiborne, A.K.; Hasvold, L.A.; Tong, Y. (Abbott Laboratories Inc.); Farnesyltransferase inhibitors. US 2002115640; WO 0274747 .
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) 57602 2-Bromo-3-methylpyridine; 2-Bromo-3-picoline 3430-17-9 C6H6BrN 详情 详情
(II) 57603 2-bromo-3-methyl-1-pyridiniumolate C6H6BrNO 详情 详情
(III) 57604 6-bromo-5-methyl-2-pyridinecarbonitrile C7H5BrN2 详情 详情
(IV) 57605 6-bromo-5-(bromomethyl)-2-pyridinecarbonitrile C7H4Br2N2 详情 详情
(V) 57606 1-methyl-5-(triethylsilyl)-1H-imidazole C10H20N2Si 详情 详情
(VI) 17552 4-formylbenzonitrile; 4-Cyanobenzaldehyde 105-07-7 C8H5NO 详情 详情
(VII) 57607 4-[hydroxy(1-methyl-1H-imidazol-5-yl)methyl]benzonitrile C12H11N3O 详情 详情
(VIII) 57608 6-bromo-5-{[(4-cyanophenyl)(1-methyl-1H-imidazol-5-yl)methoxy]methyl}-2-pyridinecarbonitrile C19H14BrN5O 详情 详情
(IX) 57609 5-Bromo-2,2-difluoro-1,3-benzodioxole;4-Bromo-1,2-[(difluoromethylene)dioxy]benzene 33070-32-5 C7H3BrF2O2 详情 详情
(X) 57610 2,2-difluoro-1,3-benzodioxol-5-ylboronic acid C7H5BF2O4 详情 详情
Extended Information