m-Chloroperbenzoic acid → HCID 67083011, compound

HRID 1892248Notes

Reaction equation

HRID 1892248 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]2[C:10]([CH3:14])=[N:11][N:12]([CH3:13])[C:5]=12)([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=[O:23])C=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-:23])=[C:6]2[C:10]([CH3:14])=[N:11][N:12]([CH3:13])[C:5]=12)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 68161400HCID 68161400, compound

Product 1

HCID 67083011HCID 67083011, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
90 °C

Procedure

To 7-isopropyl-1,3-dimethyl-1H-pyrazolo[4,3-b]pyridine (prepared in the previous step, 2.50 g, 13.22 mmol) in 100 mL of chloroform was added 77% MCPBA (5.91 g, 26.44 mmol) at 0° C. The resulting solution was stirred at 90° C. for 3 hours. After cooling, it was neutralized with aq NaHCO3 and extracted with DCM thoroughly. The combined organic phases were then washed with water, brine and concentrated. Column chromatography using 5% 7N NH3 in MeOH/DCM as eluant afforded the title compound as a white solid. Spectroscopic data: 1H-NMR (300 MHz, CDCl3): δ ppm 1.37 (d, J=6.73 Hz, 6 H), 2.83 (s, 3 H), 3.60 (hept, J=6.73 Hz, 1 H), 4.21 (s, 3 H), 6.78 (d, J=6.30 Hz, 1 H), 8.01 (d, J=6.30 Hz 1 H).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with DCM thoroughly
  3. washThe combined organic phases were then washed with water, brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-88c3ffbe97d34941a371b93c20da9869
Source dataset
uspto-grants-2013_08
Patent number
US08507682B2

Reaction notes

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