m-Chloroperbenzoic acid → 1-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline

HRID 375902Notes

Reaction equation

[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([Cl:16])=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([S:17][CH3:18])=[CH:11][CH:10]=3)[CH3:2].ClC1C=C(C=CC=1)C(OO)=[O:24].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]3[C:14]([C:15]([Cl:16])=[C:6]2[CH:5]=[N:4]1)=[CH:13][C:12]([S:17]([CH3:18])=[O:24])=[CH:11][CH:10]=3)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3, 4-b]quinoline (2.4 g, 8.7 mmol) in CHCl3 (50 mL) at -40° C. was added m-chloroperoxybenzoic acid (2.75 g, 8.7 mmol). The reaction mixture was slowly warmed to 0° C. and then saturated NaHCO3 (10 mL) was added. The reaction mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL), the layers were separated and then the aqueous layer was extracted with CH2Cl2 (20 ml). The CH2Cl2 extracts were combined, dried over MgSO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 50% ether/hexane, then 25% ethyl acetate/25% hexane/50% ether and finally ethyl acetate (100%) to afford 2.4 g of 1-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline.

Workup

customThe reaction mixture was partitioned between water (20 mL) and CH2Cl2 (20 mL)
customthe layers were separated
extractionthe aqueous layer was extracted with CH2Cl2 (20 ml)
dry with materialdried over MgSO4
customevaporated
customThe residue was purified by column chromatography on silica gel eluting with 50% ether/hexane

Sources & evidence

ORD record: ord-3e232b56fa0a4bb5a6b18888c6a443b8
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05488055

Reaction notes

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