4-bromo-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole → HCID 19436747, compound

HRID 1440136Notes

Reaction equation

[Br:1][C:2]1[C:3]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([N+:20]([O-])=O)=[CH:14][C:13]=2[F:23])=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]>C(O)(=O)C.[Fe]>[Br:1][C:2]1[C:3]([C:12]2[C:13]([F:23])=[CH:14][C:15]([NH2:20])=[C:16]([O:18][CH3:19])[CH:17]=2)=[N:4][N:5]([CH3:11])[C:6]=1[C:7]([F:10])([F:9])[F:8]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3.16 g (7.9 mmole) 4-bromo-3-(2-fluoro-5-methoxy-4-nitrophenyl)-1-methyl-5-(trifluoromethyl)-1H-pyrazole in 59 mL acetic acid was heated to 80° C. under a nitrogen atmosphere. The heat and nitrogen were removed and 1.76 g (31.6 mmole) iron powder was added in 3 portions over 5 min. The solution was stirred at 80° C. for an additional 30 min. The solution was cooled and filtered through Celite®. The filtrate was diluted with 100 mL water and extracted three times with diethyl ether. The ether extracts were washed with brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residue was purified chromatographically using 40% ethyl acetate in hexane as the eluent to give 2.4 g (83%) of 4-(4-bromo-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-5-fluoro-2-methoxy-benzeneamine as a white solid, mp 85°-86° C.

Workup

temperatureThe heat
customnitrogen were removed
temperatureThe solution was cooled
filtrationfiltered through Celite®
additionThe filtrate was diluted with 100 mL water
extractionextracted three times with diethyl ether
washThe ether extracts were washed with brine
dry with materialdried over anhydrous MgSO4
concentrationconcentrated in vacuo
customThe residue was purified chromatographically

Sources & evidence

ORD record: ord-00dbb81aba9a4ec3972e125359f1fda8
Source dataset: uspto-grants-1996_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05496956

Reaction notes

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