Sodium hydride → 2-(5-Chloro-3-Nitro-Pyridin-2-Yloxy)-1-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]Ethanone

HRID 11716ノート

反応式

HRID 11716 の反応式
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C@@H:12]([CH3:13])[CH2:11][N:10]([C:14](=[O:17])[CH2:15][OH:16])[C@H:9]([CH3:18])[CH2:8]2)=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:24]1[C:29]([N+:30]([O-:32])=[O:31])=[CH:28][C:27]([Cl:33])=[CH:26][N:25]=1>C1(C)C=CC=CC=1>[Cl:33][C:27]1[CH:28]=[C:29]([N+:30]([O-:32])=[O:31])[C:24]([O:16][CH2:15][C:14]([N:10]2[CH2:11][C@H:12]([CH3:13])[N:7]([CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:20][CH:19]=3)[CH2:8][C@H:9]2[CH3:18])=[O:17])=[N:25][CH:26]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 80633312,5-Dichloro-3-nitropyridineHCID 234058381-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone

生成物 1

HCID 696556572-(5-Chloro-3-Nitro-Pyridin-2-Yloxy)-1-[4-(4-Fluoro-Benzyl)-(2R,5S)-2,5-Dimethyl-Piperazin-1-Yl]Ethanone収率 89.4%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of 1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-hydroxy-ethanone (0.90 g, 3.2 mmol) in toluene (20 mL) at 0° C. was added sodium hydride (0.18 g, 4.5 mmol, 60% dispersion in mineral oil). The reaction was stirred for 15 minutes, then 2,5-dichloro-3-nitro-pyridine (0.65 g, 3.38 mmol) was added and the solution was stirred at ambient temperature for 18 hours. The reaction was quenched by the slow addition of water (5 mL) then extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. Flash chromatography on silica gel gave the title compound (1.25 g).

後処理

  1. stirringthe solution was stirred at ambient temperature for 18 hours
  2. customThe reaction was quenched by the slow addition of water (5 mL)
  3. extractionthen extracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2a0344112e3c4eae845fa2698f0127bd
出典データセット
uspto-grants-2006_08
特許番号
US07098212B2

反応ノート

読み込み中…