1-Phenylpyrazol-5-ylamine → 5-Bromo-1-phenyl-1H-pyrazolo[3,4-b]pyridine

HRID 1787579Notes

Reaction equation

HRID 1787579 reaction equation
[C:1]1([N:7]2[C:11]([NH2:12])=[CH:10][CH:9]=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:13][CH:14]([CH:17]=O)[CH:15]=O>C(O)(=O)C>[Br:13][C:14]1[CH:15]=[C:10]2[CH:9]=[N:8][N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:11]2=[N:12][CH:17]=1

Participants

4

Reactant 2

HCID 700061-Phenylpyrazol-5-ylamineHCID 749452-Bromopropanedial

Product 1

HCID 576003615-Bromo-1-phenyl-1H-pyrazolo[3,4-b]pyridineYield 28.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolve 1-phenyl-5-aminopyrazole (Tokyo Kasei Kogyo Co. LTD; 1.5 g, 9.4 mmol) and 2-bromomalonaldehyde (Aldrich; 1.42 g, 9.4 mmol) in glacial acetic acid (170 mL) and reflux under nitrogen for 5 h. Concentrate under reduced pressure and purify via chromatography (silica gel, dichloromethane) to obtain 740 mg (28%) of the title compound as an off-white solid. TOF MS ES+ exact mass calculated for C12H9N3Br (p+H): m/z=273.9980, Found. 273.9965.

Workup

  1. temperaturereflux under nitrogen for 5 h
  2. concentrationConcentrate under reduced pressure
  3. custompurify via chromatography (silica gel, dichloromethane)

Sources & evidence

ORD record
ord-dd53d6932502484faa6025be9add0023
Source dataset
uspto-grants-2009_03
Patent number
US07511056B2

Reaction notes

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