Trifluoroacetic acid → 4-Iodo-1-methyl-5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1H-pyrazole
Reaction equation
[I:1]N1C(=O)CCC1=O.FC(F)(F)C(O)=O.[CH3:16][N:17]1[C:21]([CH2:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[CH:20][CH:19]=[N:18]1>>[I:1][C:20]1[CH:19]=[N:18][N:17]([CH3:16])[C:21]=1[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:32])([F:31])[F:33])=[CH:26][CH:25]=1Participants
Procedure
N-iodosuccinimide (1.91 g) was added to a trifluoroacetic acid (15 mL) solution of 1-methyl-5-{2-[4-(trifluoromethyl)phenyl]ethyl}-1H-pyrazole (1.96 g) at a room temperature, and the obtained solution was then stirred for 1 hour. Thereafter, the reaction solution was concentrated under a reduced pressure, and the residue was then diluted with chloroform. The resultant was washed with a saturated sodium hydrogencarbonate aqueous solution/a 30% sodium thiosulfate aqueous solution (1:1). The organic layer was washed with a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=70:30 to 50:50), so as to obtain the title compound (2.98 g) in the form of a colorless oily substance.
Workup
- concentrationThereafter, the reaction solution was concentrated under a reduced pressure
- additionthe residue was then diluted with chloroform
- washThe resultant was washed with a saturated sodium hydrogencarbonate aqueous solution/a 30% sodium thiosulfate aqueous solution (1:1)
- washThe organic layer was washed with a saturated saline
- dry with materialwas then dried over anhydrous magnesium sulfate
- concentrationfollowed by vacuum concentration
- customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=70:30 to 50:50)
Sources & evidence
- ORD record
- ord-021a6f93151345b6a9a681c011395d1d
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642626B2
Reaction notes
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