Triethylamine → 1-(2-Fluorophenyl)-5-iodo-1H-pyrazol-3-ylamine

HRID 83540Notes

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-(2,5-dimethylpyrrol-1-yl)-1-(2-fluorophenyl)-5-iodo-1H-pyrazole (1.23 g) in ethanol/water (2/1, 18 ml) were sequentially added hydroxylammonium chloride (4.47 g) and triethylamine (0.9 ml) at room temperature, and the mixture was stirred at 90° C. for 24 hours. This reaction mixture was cooled to room temperature, concentrated under reduced pressure. To the resulting residue was added a 8M aqueous solution of sodium hydroxide, and then the mixture was extracted with ethyl acetate. This organic layer was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 1/1) to give the titled compound (0.61 g).

Workup

customat room temperature
temperatureThis reaction mixture was cooled to room temperature
concentrationconcentrated under reduced pressure
additionTo the resulting residue was added a 8M aqueous solution of sodium hydroxide
extractionthe mixture was extracted with ethyl acetate
washThis organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1 to 1/1)

Sources & evidence

ORD record: ord-10bb6928f08c4fd7afbbd1555a15c81a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846746B2

Reaction notes

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