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

HRID 1586186Notes

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. is added m-chloroperoxybenzoic acid (2.75 g, 8.7 mmol). The reaction mixture is slowly warmed to 0° C. and then saturated NaHCO3 (10 ml) is added. The reaction mixture is partitioned between water (20 ml) and CH2Cl2 (20 ml), the layers are separated and then the aqueous layer is extracted with CH2Cl2 (20 ml). The CH2Cl2 extracts are combined, dried over MgSO4 and evaporated. The residue is 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 is partitioned between water (20 ml) and CH2Cl2 (20 ml)
customthe layers are separated
extractionthe aqueous layer is extracted with CH2Cl2 (20 ml)
dry with materialdried over MgSO4
customevaporated
customThe residue is purified by column chromatography on silica gel eluting with 50% ether/hexane

Sources & evidence

ORD record: ord-98eddf10ab54442bbb3585dbeec25967
Source dataset: uspto-grants-1999_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05942520

Reaction notes

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