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【结 构 式】

【分子编号】51953

【品名】N-(2-phenyl-3-pyridinyl)acetamide

【CA登记号】

【 分 子 式 】C13H12N2O

【 分 子 量 】212.25116

【元素组成】C 73.57% H 5.7% N 13.2% O 7.54%

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:(IV)

The 2-phenylpyridine-3-amine (V), an intermediate in the synthesis of 235944, has been obtained with better yields by three related ways: 1. The acylation of 2-chloropyridine-3-amine (I) with Ac2O and TEA in dichloromethane gives the corresponding acetamide (II), which is condensed with phenylboronic acid (III) by means of Pd(PPh3)4 and Na2CO3 in ethanol/toluene, yielding N-(2-phenylpyridin-3-yl)acetamide (IV). Finally, this compound is hydrolyzed with HCl in methanol to afford the target 2-phenylpyridine-3-amine (V) intermediate. 2. The condensation of 2-chloropyridine-3-amine (I) with benzaldehyde (VI) in refluxing toluene gives the corresponding imine (VII), which is condensed with phenylboronic acid (III) as before to yield the 2-phenylpyridine derivative (VIII). Finally, the imino group of (VIII) is hydrolyzed with aqueous HCl to afford the target intermediate (V). 3. The one-pot condensation of 2-chloropyridine-3-amine (I), boronic acid (III) and benzaldehyde (VI) by means of Pd(PPh3)2Cl2 and Na2CO3 in hot toluene gives the already reported 2-phenylpyridine derivative (VIII), which is hydrolyzed as before to afford the target intermediate (V).

1 Caron, S.; et al.; An efficient and cost-effective synthesis of 2-phenyl-3-aminopyridine. Org Process Res Dev 2001, 5, 3, 254.
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) 11160 2-Chloro-3-pyridinamine; 2-Chloro-3-pyridinylamine; 3-Amino-2-chloropyridine; 2-Chloro-3-aminopyridine 6298-19-7 C5H5ClN2 详情 详情
(II) 51952 N-(2-Chloropyridin-3-yl)acetamide C7H7ClN2O 详情 详情
(III) 16593 Phenylboronic acid;Benzeneboronic acid;Phenylboron dihydroxide 98-80-6 C6H7BO2 详情 详情
(IV) 51953 N-(2-phenyl-3-pyridinyl)acetamide C13H12N2O 详情 详情
(V) 51954 2-phenyl-3-pyridinylamine; 2-phenyl-3-pyridinamine C11H10N2 详情 详情
(VI) 10498 Benzaldehyde;Benzoic aldehyde;Phenylmethanal 100-52-7 C7H6O 详情 详情
(VII) 51955 N-(2-chloro-3-pyridinyl)-N-[(E)-benzylidene]amine; 2-chloro-N-[(E)-benzylidene]-3-pyridinamine C12H9ClN2 详情 详情
(VIII) 51956 2-phenyl-N-[(E)-benzylidene]-3-pyridinamine; N-[(E)-benzylidene]-N-(2-phenyl-3-pyridinyl)amine C18H14N2 详情 详情
Extended Information