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

HRID 573350Notes

Reaction equation

HRID 573350 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][CH:20]=[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.[NH2:25][NH2:26]>CCO>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[NH:26][N:25]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86688990[4-(Benzyloxy)phenyl](3-fluoropyridin-2-yl)methanone

Product 1

HCID 866889913-[4-(Benzyloxy)phenyl]-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of [4-(benzyloxy)phenyl](3-fluoropyridin-2-yl)methanone (3.0 g) and hydrazine hydrate (5.0 mL) in EtOH (90 mL) was refluxed for 4 days. The mixture was concentrated under reduced pressure. The residue was partitioned between water and AcOEt. The organic layer was washed with brine, dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (0.83 g).

Workup

  1. temperaturewas refluxed for 4 days
  2. concentrationThe mixture was concentrated under reduced pressure
  3. customThe residue was partitioned between water and AcOEt
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-e92d2b14f37e4ec791e3f6ffcac5340b
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

Loading…