Water → 3-(3-fluorophenyl)-1H-pyrazolo[4,3-b]pyridine
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([C:10]2[C:15](F)=[CH:14][CH:13]=[CH:12][N:11]=2)=O)[CH:5]=[CH:6][CH:7]=1.O.[NH2:18][NH2:19].O>CO>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:15]3[NH:19][N:18]=2)[CH:5]=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
1.5 g of (3-fluorophenyl)-(3-fluoropyridin-2-yl)-methanone was dissolved in 5 mL of methanol, added with 1.0 mL of hydrazine monohydrate, and heated at 80° C. for 4 hours. The reaction solution was added with water, and extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the residue was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:4), to afford 240 mg of the title compound as a colorless powder.
Workup
- extractionextracted with ethyl acetate
- washThe organic layer was washed successively with water and saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
- customthe residue was purified
- customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:4)
Sources & evidence
- ORD record
- ord-ab132e1377fb4a9390315de1c1e71b20
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07429609B2
Reaction notes
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