Hydrazine hydrate (1:1) → 3-[5-(Benzyloxy)pyridin-2-yl]-1H-pyrazolo[4,3-b]pyridine

HRID 573323Notes

Reaction equation

HRID 573323 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]([C:17]2[C:22](F)=[CH:21][CH:20]=[CH:19][N:18]=2)=O)=[N:13][CH:14]=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:10]=[CH:11][C:12]([C:15]2[C:17]3=[N:18][CH:19]=[CH:20][CH:21]=[C:22]3[NH:26][N:25]=2)=[N:13][CH:14]=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 86688982[5-(Benzyloxy)pyridin-2-yl](3-fluoropyridin-2-yl)methanone

Product 1

HCID 667277533-[5-(Benzyloxy)pyridin-2-yl]-1H-pyrazolo[4,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of [5-(benzyloxy)pyridin-2-yl] (3-fluoropyridin-2-yl)methanone (2.85 g) and hydrazine monohydrate (1.348 mL) in EtOH (10 mL) was stirred at 50° C. overnight. After cooling, insoluble material was filtrated and washed with EtOH. The filtrate was evaporated, treated with water and extracted with AcOEt. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (0.232 g).

Workup

  1. temperatureAfter cooling
  2. filtrationinsoluble material was filtrated
  3. washwashed with EtOH
  4. customThe filtrate was evaporated
  5. additiontreated with water
  6. extractionextracted with AcOEt
  7. dry with materialThe organic layer was dried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Sources & evidence

ORD record
ord-09bb524c75bb43a7886b07b9575861bf
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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