m-Chloroperbenzoic acid → 3-Methyl-4-(propylsulfinyl)-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 498023Notes

Reaction equation

HRID 498023 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH3:12][C:13]1[C:25]2[C:16](=[N:17][C:18]3[C:23]([C:24]=2[S:26][CH2:27][CH2:28][CH3:29])=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:14]=1>C(Cl)(Cl)Cl>[CH3:12][C:13]1[C:25]2[C:16](=[N:17][C:18]3[C:23]([C:24]=2[S:26]([CH2:27][CH2:28][CH3:29])=[O:9])=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:15]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:14]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 223201473-Methyl-4-(propylsulfanyl)-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline

Product 1

HCID 223201693-Methyl-4-(propylsulfinyl)-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinolineYield 52.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (0.96 g, 5.6 mmol) in chloroform (55 mL) was added dropwise to a solution of 3-methyl-4-propylsulfanyl-1-(2-pyridinyl)-1H-pyrazolo[3,4-b]quinoline (1.54 g, 4.6 mmol) in chloroform (55 mL) at a temperature of lower than 0° C., and the mixture was stirred at the same temperature for another 2.5 hours. The reaction solution was washed with an aqueous saturated sodium bicarbonate solution and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue thus obtained was purified by silica gel column chromatography (hexane:chloroform:ethyl acetate=2:1:1 to 1:1:1) to give the title compound (0.84 g, 52% yield).

Workup

  1. washThe reaction solution was washed with an aqueous saturated sodium bicarbonate solution and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue thus obtained
  5. customwas purified by silica gel column chromatography (hexane:chloroform:ethyl acetate=2:1:1 to 1:1:1)

Sources & evidence

ORD record
ord-0882127f6b3947f9b8e23ad2697a0c10
Source dataset
uspto-grants-2005_09
Patent number
US06949648B2

Reaction notes

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