1-Butanol → HCID 66614473, compound
Reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].[H-].[Na+].F[C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[N:19]([CH3:20])[C:18]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[CH:24][C:17]=2[N:16]=1.[Cl-].[NH4+]>CN(C=O)C>[CH2:1]([O:5][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:14]=1[C:15]1[N:19]([CH3:20])[C:18]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[CH:24][C:17]=2[N:16]=1)[CH2:2][CH2:3][CH3:4]Participants
Procedure
To a mixture of 0.44 g of 1-butanol 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. And, 2-(3-fluoropyridin-4-yl-)-1-methyl-5-trifluoromethyl-1H-benzimidazole (0.35 g) was added, then, the mixture was stirred for 1.5 hours at room temperature. Into the reaction mixture was poured a saturated ammonium chloride aqueous solution, and the mixture was extracted three times with ethyl acetate. The organic layer was dried over magnesium sulfate, then, concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, to obtain 0.37 g of 2-(3-butoxypyridin-4-yl-)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter, referred to as present active compound 206).
Workup
- temperaturecool
- stirringthe mixture was stirred for 1.5 hours at room temperature
- extractionthe mixture was extracted three times with ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-09d2ad4134914689842395a07cff173e
- Source dataset
- uspto-grants-2013_06
- Patent number
- US08461181B2
Reaction notes
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