p-Toluenesulfonic acid → 5-Bromopyrazolo[3,4-b]pyridine

HRID 2092265Notes

Reaction equation

HRID 2092265 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](F)=[C:6]([CH:9]=1)[CH:7]=O.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:22][NH2:23]>CC(O)C.O>[Br:1][C:2]1[CH:9]=[C:6]2[CH:7]=[N:23][NH:22][C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9321HydrazineHCID 454801925-Bromo-2-fluoro-3-pyridinecarboxaldehyde

Product 1

HCID 404274545-Bromopyrazolo[3,4-b]pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 5-bromo-2-fluoronicotinaldehyde (0.580 g, 2.8 mmol), 4-methylbenzenesulfonic acid (0.060 g, 0.35 mmol) and anhydrous hydrazine (0.450 ml, 14 mmol) in 5 mL of i-PrOH was heated at 145° C. for 15 min in the microwave (Initiator by Biotage). The reaction was diluted with H2O and the solid was filtered washed with H2O and air-dried to give a white amorphous solid. MS (M+H)+ 198, 200.

Workup

  1. filtrationthe solid was filtered
  2. washwashed with H2O
  3. customair-dried
  4. customto give a white amorphous solid

Sources & evidence

ORD record
ord-27a78b77ed214417b9b4546aaba7f86f
Source dataset
uspto-grants-2013_05
Patent number
US08440674B2

Reaction notes

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