2-Bromopropanedial → 5-Bromo-1-methyl-1H-pyrazolo(3,4-b)pyridine

HRID 1787580Notes

Reaction equation

HRID 1787580 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[CH:5][CH:4]=[N:3]1.[Br:8][CH:9]([CH:12]=O)[CH:10]=O>C(O)(=O)C>[Br:8][C:9]1[CH:10]=[C:5]2[CH:4]=[N:3][N:2]([CH3:1])[C:6]2=[N:7][CH:12]=1

Participants

4

Reactant 2

HCID 749452-BromopropanedialHCID 1369272-Methyl-2H-pyrazol-3-ylamine

Product 1

HCID 574158895-Bromo-1-methyl-1H-pyrazolo(3,4-b)pyridineYield 27.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Dissolve 1-methyl-5-aminopyrazole (Butt Park LTD; 1.0 g, 10.3 mmol) and 2-bromomalonaldehyde (Aldrich; 1.55 g, 10.3 mmol) in glacial acetic acid (160 mL) and reflux under nitrogen for 48 h. Concentrate under reduced pressure and purify via chromatography (silica gel, 90% dichloromethane/10% diethyl ether) to obtain 610 mg (27%) of the title compound as an off-white solid. TOF MS ES+ exact mass calculated for C7H7N3Br (p+H): m/z=211.9823, Found: 211.9838.

Workup

  1. temperaturereflux under nitrogen for 48 h
  2. concentrationConcentrate under reduced pressure
  3. custompurify via chromatography (silica gel, 90% dichloromethane/10% diethyl ether)

Sources & evidence

ORD record
ord-55273c1aa3e34e979796e4e2114b3cbe
Source dataset
uspto-grants-2009_03
Patent number
US07511056B2

Reaction notes

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