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Hydrazine hydrate (1:1) → 3-[4-(Benzyloxy)phenyl]-6-fluoro-1H-pyrazolo[4,3-b]pyridine

HRID 573364
Notes
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Reaction equation

HRID 573364 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][C:20]([F:24])=[CH:19][N:18]=2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:26][NH2:27].C([O-])(O)=O.[Na+]>CC(O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:17]3=[N:18][CH:19]=[C:20]([F:24])[CH:21]=[C:22]3[NH:27][N:26]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 516892Sodium BicarbonateHCID 66727888[4-(Benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone

Product 1

HCID 667280483-[4-(Benzyloxy)phenyl]-6-fluoro-1H-pyrazolo[4,3-b]pyridineYield 79.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of [4-(benzyloxy)phenyl](3,5-difluoropyridin-2-yl)methanone (41 mg), hydrazine hydrate (31.5 mg) and 2-propanol (10 mL) was stirred at 90° C. for 12 h, treated with saturated NaHCO3 aqueous solution, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (32.0 mg).

Workup

  1. extractionextracted with AcOEt
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-44dc867bf5fa4d839550d5b00f315adf
Source dataset
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09029536B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes