(Chloromethyl)dimethylisopropoxysilane → 1-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-(isopropoxy-dimethyl-silanyl)-ethanol

HRID 216483ノート

反応式

HRID 216483 の反応式
Cl[CH2:2][Si:3]([CH3:9])([CH3:8])[O:4][CH:5]([CH3:7])[CH3:6].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19]([CH:28]=[O:29])=[CH:20][C:21]3[NH:25][CH:24]=[N:23][C:22]=3[C:26]=2[F:27])=[C:13]([Cl:30])[CH:12]=1>C1COCC1>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19]([CH:28]([OH:29])[CH2:2][Si:3]([O:4][CH:5]([CH3:7])[CH3:6])([CH3:9])[CH3:8])=[CH:20][C:21]3[NH:25][CH:24]=[N:23][C:22]=3[C:26]=2[F:27])=[C:13]([Cl:30])[CH:12]=1

参加物

4

反応物 2

HCID 266137(Chloromethyl)dimethylisopropoxysilaneHCID 112456086-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carbaldehyde

生成物 1

HCID 211141671-[6-(4-Bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazol-5-yl]-2-(isopropoxy-dimethyl-silanyl)-ethanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-78 °C

実験手順

To a solution of the Grignard reagent prepared from Mg and chloromethyl dimethylisopropoxy silane (Org. Synth. 1992, 69, 96) [4.4 mL, 3.26 mmol, 0.74 M solution (based on 90% purity)] in THF, is added a solution of 6-(4-bromo-2-chloro-phenylamino)-7-fluoro-3H-benzoimidazole-5-carbaldehyde 10f (200 mg, 0.54 mmol) in THF (1 mL) at −78° C. After stirring for 1 hour at −78° C., the reaction is quenched with saturated aqueous NH4Cl, and extracted with EtOAc. The organic layer is dried over MgSO4, filtered, concentrated in vacuo to afford the crude desired product which is directly used without further purification.

後処理

  1. customthe reaction is quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-2d26fa556f4f4cb68589731861a58e36
出典データセット
uspto-grants-2012_06
特許番号
US08193229B2

反応ノート

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