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

HRID 253472

Reaction equation

[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

Participants

Conditions

Temperature: 80 °C

Procedure

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%).

Workup

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

Sources & evidence

ORD record: ord-b67791df0d85411bb791426b835e2076
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07872018B2

Linked notes

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