Water → HCID 89586330, compound

HRID 1747762Notes

Reaction equation

HRID 1747762 reaction equation
Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7](=[O:26])[C:8](=[N:12][NH:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH:24]=[CH:23][CH:22]=[N:21]2)=[CH:16][C:15]=1[F:25])[C:9](=[O:11])[CH3:10].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[C:9]([C:8]1[C:7](=[O:26])[C:3]2[O:4][CH:5]=[CH:6][C:2]=2[N:13]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH:24]=[CH:23][CH:22]=[N:21]3)=[CH:16][C:15]=2[F:25])[N:12]=1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 178468349HCID 178468349, compound

Product 1

HCID 89586330HCID 89586330, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 1-(3-bromofuran-2-yl)-2-{[2-fluoro-4-(1H-pyrazol-1-yl)phenyl]hydrazono}butane-1,3-dione (5.3 g) and potassium carbonate (3.5 g) in DMF (40 mL) was stirred at 90° C. for 4 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was suspended in diisopropylether, and the precipitate was collected by filtration to give the title compound (2.56 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4a4bef041ca043dc838e3f5086a49e14
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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