1-Propanol → 1-methyl-2-(3-propoxypyridin-4-yl)-5-trifluoromethyl-1H-benzimidazole
Reaction equation
[CH2:1]([OH:4])[CH2:2][CH3:3].[H-].[Na+].F[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[C:14]1[N:18]([CH3:19])[C:17]2[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:16]=2[N:15]=1.[Cl-].[NH4+]>CN(C=O)C>[CH3:19][N:18]1[C:17]2[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:16]=2[N:15]=[C:14]1[C:13]1[CH:12]=[CH:11][N:10]=[CH:9][C:8]=1[O:4][CH2:1][CH2:2][CH3:3]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of 0.36 g of 1-propanol and 6 ml of DMF was added 0.24 g of 60% sodium hydride (oily) under ice cool, and the mixture was stirred for 10 minutes. 2-(3-fluoropyridin-4-yl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (0.35 g) was added, then, the mixture was heated up to room temperature and further stirred for 1 hour. A saturated ammonium chloride aqueous solution was poured, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 0.36 g of 1-methyl-2-(3-propoxypyridin-4-yl)-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 10).
Workup
- temperaturecool
- stirringfurther stirred for 1 hour
- extractionthe mixture was extracted three times with ethyl acetate
- dry with materialThe combined organic layers were dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-fae2ba95057d4df8b5bf7a4ceee39964
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08273764B2
Reaction notes
Loading…