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4-Methoxybenzylamine → N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridin-2-amine

HRID 253959
ノート
印刷プレビュー

反応式

HRID 253959 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.[Br:11][C:12]1[CH:13]=[C:14]([C:19]2[N:20]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=3[Cl:31])[CH:21]=[CH:22][N:23]=2)[C:15](Cl)=[N:16][CH:17]=1>O1CCOCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:15]2[C:14]([C:19]3[N:20]([C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[C:25]=4[Cl:31])[CH:21]=[CH:22][N:23]=3)=[CH:13][C:12]([Br:11])=[CH:17][N:16]=2)=[CH:5][CH:4]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 754524-MethoxybenzylamineHCID 581798675-bromo-2-chloro-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridine

生成物 1

HCID 58180101N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridin-2-amine

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
100 °C

実験手順

To a solution of excess (4-methoxyphenyl)methanamine (0.2 mL) in dioxane (2 mL) was added 5-bromo-2-chloro-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridine (0.089 g, 0.222 mmol). The mixture was heated at 100° C. for 16 hours in a sealed reaction vessel. The mixture was then cooled, diluted with ethyl acetate, washed with saturated aqueous sodium bicarbonate, and the combined organics dried over sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography (20% hexanes/methylene chloride to 25% ethyl acetate/methylene chloride to provide 0.065 g of N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-dichlorophenyl)-1H-imidazol-2-yl)pyridin-2-amine [LC-MS m/e=505.0 (M+H)]. Using the same procedure, N-(4-methoxybenzyl)-5-bromo-3-(1-(2,3-difluorophenyl)-1H-imidazol-2-yl)pyridin-2-amine and N-(4-methoxybenzyl)-5-bromo-3-(1-(3-chloro-2-fluorophenyl)-1H-imidazol-2-yl)pyridin-2-amine can be produced from 5-bromo-2-chloro-3-(1-(2,3-difluorophenyl)-1H-imidazol-2-yl)pyridine and 5-bromo-2-chloro-3-(1-(3-chloro-2-fluorophenyl)-1H-imidazol-2-yl)pyridine, respectively

後処理

  1. temperatureThe mixture was then cooled
  2. washwashed with saturated aqueous sodium bicarbonate
  3. dry with materialthe combined organics dried over sodium sulfate
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by flash chromatography (20% hexanes/methylene chloride to 25% ethyl acetate/methylene chloride

出典と根拠

ORDレコード
ord-4c3fe3aec15844f6a495ef6fff711e5f
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07872031B2

反応ノート

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