Triethylamine → 1-(3-Fluorophenyl)-5-iodo-1H-pyrazol-3-ylamine

HRID 83499Notes

Reaction equation

CC1[N:3]([C:8]2[CH:12]=[C:11]([I:13])[N:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)[N:9]=2)C(C)=CC=1.[Cl-].O[NH3+].C(N(CC)CC)C>CCCCCC.C(OCC)(=O)C>[F:20][C:16]1[CH:15]=[C:14]([N:10]2[C:11]([I:13])=[CH:12][C:8]([NH2:3])=[N:9]2)[CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 95 °C

Procedure

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-(3-fluorophenyl)-5-iodo-1H-pyrazole (4.5 g) in ethanol/water (2/1, 81 ml) were sequentially added hydroxylammonium chloride (16.3 g) and triethylamine (3.3 ml), and the mixture was stirred at 95° C. for 17 hours. This reaction mixture was cooled to room temperature and concentrated under reduced pressure. To the resulting residue was added an 8M aqueous solution of sodium hydroxide, and the mixture was extracted with ethyl acetate. This organic layer was sequentially washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1) to give the titled compound (3.2 g).

Workup

temperatureThis reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
additionTo the resulting residue was added an 8M aqueous solution of sodium hydroxide
extractionthe mixture was extracted with ethyl acetate
washThis organic layer was sequentially washed with water
dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record: ord-4958583d39724c58a3f05e282281cb19
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846746B2

Reaction notes

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