m-Chloroperbenzoic acid → HCID 10291593, compound

HRID 2214921Notes

Reaction equation

HRID 2214921 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([S:16][CH3:17])[N:10]3[N:9]=2)=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:33])C=1.CCCCCC.C(OCC)(=O)C>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:18]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][N:20]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[C:15]([S:16]([CH3:17])=[O:33])[N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 9945696HCID 9945696, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 10291593HCID 10291593, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of 2-(4-fluorophenyl)-7-methylthio-3-(4-pyrimidinyl)pyrazolo[1,5-α]pyridine (Example 6, 0.246 g, 0.73 mmol) in chloroform (20 mL) was added, dropwise, a solution of of m-chloroperbenzoic acid (57–86%, 0.221 g, 0.73–1.1 mmol) in chloroform (10 mL). After 1 hour, the reaction was quenched by the addition of aqueous potassium carbonate (20 mL), and the organic phase was separated. The aqueous phase was further extracted with chloroform (2×20 mL) and the combined chloroform phases were dried over anhydrous magnesium sulfate. The drying agent was removed by filtration and the solvent was evaporated to give a light brown solid. Chromatography on silica gel eluting with a hexane/ethyl acetate gradient (0–30% ethyl acetate) gave the title compound as the major product, 0.170 g (66%). 1H NMR (DMSO-d6): δ 3.11 (s, 3H), 7.13 (d, J=5.4 Hz, 1H), 7.33 (t, J=8.8 Hz, 2H), 7.50 (d, J=7.0 Hz, 1H), 7.63 (dd, J=5.7, 8.6 Hz, 2H), 7.76 (dd, J=7.4, 8.1 Hz, 1H), 8.50 (d, J=8.8 Hz, 1H), 8.60 (d, J=5.5 Hz, 1H). 9.20 (s, 1H), APESI+MS m/z 353 (M+1)−.

Workup

  1. customthe reaction was quenched by the addition of aqueous potassium carbonate (20 mL)
  2. customthe organic phase was separated
  3. extractionThe aqueous phase was further extracted with chloroform (2×20 mL)
  4. dry with materialthe combined chloroform phases were dried over anhydrous magnesium sulfate
  5. customThe drying agent was removed by filtration
  6. customthe solvent was evaporated
  7. customto give a light brown solid

Sources & evidence

ORD record
ord-1ef4ab4f160541a0bbdd8bdcdf45e4e8
Source dataset
uspto-grants-2006_09
Patent number
US07109209B2

Reaction notes

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