Sodium hydride → 4-(5,6-Dichloro-1-benzoimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde

HRID 253472

反応式

HRID 253472 の反応式
[F:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:3]=1[CH:4]=[O:5].[H-].[Na+].[Cl:16][C:17]1[C:27]([Cl:28])=[CH:26][C:20]2[NH:21][C:22](CCl)=[N:23][C:19]=2[CH:18]=1>CN(C)C=O>[Cl:28][C:27]1[C:17]([Cl:16])=[CH:18][C:19]2[N:23]=[C:22]([CH2:11][O:10][C:8]3[C:7]([O:12][CH3:13])=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([F:1])[CH:9]=3)[NH:21][C:20]=2[CH:26]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 38349Benzimidazole, 2-chloromethyl-5,6-dichloro-HCID 6035952-Fluoro-4,5-dimethoxybenzaldehyde

生成物 1

HCID 598038814-(5,6-Dichloro-1-benzoimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

2-Fluoro-4-hydroxy-5-methoxy-benzaldehyde (38, 0.364 g, 2.14 mmol) was dissolved in N,N-dimethylformamide (10.0 mL) and sodium hydride (60% dispersion in mineral oil, 100 mg, 2.50 mmol) was added. After 20 minutes, 5,6-dichloro-2-chloromethyl-1H-benzoimidazole (208, 0.420 g, 1.78 mmol) was added. The reaction was stirred at 80° C. overnight. The reaction was concentrated, then washed with ethyl acetate and saturated sodium bicarbonate. The organic portions were dried with anhydrous sodium sulfate, filtered and the filtrate was adsorbed onto silica. The mixture was purified by silica gel chromatography, eluting with methanol/dichloromethane, to provide the desired compound, consistent by 1H-NMR (209, 140 mg, 21%).

後処理

  1. concentrationThe reaction was concentrated
  2. washwashed with ethyl acetate and saturated sodium bicarbonate
  3. dry with materialThe organic portions were dried with anhydrous sodium sulfate
  4. filtrationfiltered
  5. customThe mixture was purified by silica gel chromatography
  6. washeluting with methanol/dichloromethane

出典と根拠

ORDレコード
ord-b67791df0d85411bb791426b835e2076
出典データセット
uspto-grants-2011_01
特許番号
US07872018B2

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