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Water → 3-(3-fluorophenyl)-1H-pyrazolo[4,3-b]pyridine

HRID 34000
Notes
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Reaction equation

HRID 34000 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]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 23070169(3-Fluorophenyl)-(3-fluoropyridin-2-yl)-methanone

Product 1

HCID 100134493-(3-fluorophenyl)-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed successively with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:4)

Sources & evidence

ORD record
ord-ab132e1377fb4a9390315de1c1e71b20
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429609B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes