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Sodium borohydride → 1-{5-Chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-ethanol

HRID 912880
ノート
印刷プレビュー

反応式

HRID 912880 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:27](=[O:29])[CH3:28])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:13][CH2:12][N:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:26])([F:25])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:10][CH2:9]1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:27]([OH:29])[CH3:28])[CH:5]=[N:6][C:7]=1[N:8]1[CH2:9][CH2:10][N:11]([C:14]2[NH:18][C:17]3[CH:19]=[C:20]([C:23]([F:25])([F:26])[F:24])[CH:21]=[CH:22][C:16]=3[N:15]=2)[CH2:12][CH2:13]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

4

反応物 2

HCID 4311764Sodium borohydrideHCID 104774141-(5-chloro-6-(4-(5-(trifluoromethyl)-1H-benzo[d]imidazol-2-yl)piperazin-1-yl)pyridin-3-yl)ethanone

生成物 1

HCID 117188331-{5-Chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-ethanol

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-{5-chloro-6-[4-(6-trifluoromethyl-1H-benzoimidazol-2-yl)-piperazin-1-yl]-pyridin-3-yl}-ethanone (0.3 g, 0.71 mmol, Example 97e) in MeOH (20 mL) was added portionwise NaBH4 (0.037 g, 1.0 mmol, Aldrich) with stirring at 0° C. The reaction mixture was stirred at 0° C. for 30 min, quenched with 20 mL of satd. aq. NaHCO3, and diluted with EtOAc (50 mL). The organic phase was separated, washed with brine (20 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from 1:1 EtOAc/hexane mixture to give the title compound as a white foam. MS (ESI, pos. ion) m/z: 426 (M+1).

後処理

  1. stirringThe reaction mixture was stirred at 0° C. for 30 min
  2. customquenched with 20 mL of satd
  3. additionaq. NaHCO3, and diluted with EtOAc (50 mL)
  4. customThe organic phase was separated
  5. washwashed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from 1:1 EtOAc/hexane mixture

出典と根拠

ORDレコード
ord-4fa6e2b1ee8d45b5a8991e4e638ed6e3
出典データセット
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08026241B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート