Hydrazine hydrate (1:1) → 3-amino-5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridine

HRID 2213072Notes

Reaction equation

HRID 2213072 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=2[F:20])=[N:7][CH:6]=1>N1C=CC=CC=1>[F:20][C:14]1[C:15]([F:19])=[CH:16][CH:17]=[CH:18][C:13]=1[C:8]1[CH:9]=[C:10]2[C:11]([NH2:12])=[N:3][NH:2][C:5]2=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219565075-Chloro-2-(2,3-difluorophenyl)isonicotinonitrile

Product 1

HCID 219482673-amino-5-(2,3-difluorophenyl)-1H-pyrazolo[3,4-c]pyridine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrazine hydrate (0.52 ml, 10.7 mmol) was added to a stirred solution of 5-chloro-2-(2,3-difluorophenyl)isonicotinonitrile (1.22 g, 4.9 mmol) in pyridine (12.5 mL). The reaction mixture was stirred at reflux for 2 hours, allowed to cool and concentrated. Purification by column chromatography using a gradient of 5–10% methanol in dichloromethane as eluent afforded the title compound as a solid.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureto cool
  3. concentrationconcentrated
  4. customPurification by column chromatography

Sources & evidence

ORD record
ord-031a34602d1d4131a45b0ef28842f8d7
Source dataset
uspto-grants-2006_09
Patent number
US07105532B2

Reaction notes

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