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

HRID 253472

반응식

HRID 253472 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-b67791df0d85411bb791426b835e2076
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872018B2

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