Reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][O:11][C:12]1[C:19]([O:20][CH3:21])=[CH:18][C:15]([CH:16]=[O:17])=[C:14]([F:22])[CH:13]=1.[CH3:23]N(C)C=O.[H-].[Na+].CI>>[F:22][C:14]1[CH:13]=[C:12]([O:11][CH2:10][C:2]2[N:3]([CH3:23])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[N:1]=2)[C:19]([O:20][CH3:21])=[CH:18][C:15]=1[CH:16]=[O:17]Participants
Procedure
4-(1H-Benzimidazol-2-ylmethoxy)-2-fluoro-5-methoxy-benzaldehyde (142) (0.600 g, 2.0 mmol) was dissolved in N,N-dimethylformamide (15 mL, 190 mmol). After the addition of sodium hydride (60% dispersion in oil, 0.072 g, 3.0 mmol) the reaction was stirred for 15 minutes at room temperature. Methyl iodide (140 μL, 2.2 mmol) was added dropwise to the mixture. The reaction was stirred overnight at room temperature under an atmosphere of nitrogen. The solvent was evaporated to dryness under reduced pressure. Ethyl acetate was added and the organic portion was washed with water, dried over anhydrous sodium sulfate and concentrated. Purification with silica gel flash chromatography with a gradient of ethyl acetate in hexanes gave the desired compound as a white powder (143, 0.345 g, 55%). MS (ESI) [M+H+]+=315.2.
Workup
- stirringThe reaction was stirred overnight at room temperature under an atmosphere of nitrogen
- customThe solvent was evaporated to dryness under reduced pressure
- additionEthyl acetate was added
- washthe organic portion was washed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated
- customPurification with silica gel flash chromatography with a gradient of ethyl acetate in hexanes
Sources & evidence
- ORD record
- ord-ed92e1fe79da49eaaf7820498ab0b543
- Source dataset
- uspto-grants-2011_01
- Patent number
- US07872018B2
Linked notes
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