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

HRID 375902노트

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HRID 375902 반응식
[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]

참가 물질

5

반응물 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 212177171-ethyl-4-chloro-6-(methylthio)-1H-pyrazolo[3,4-b]quinoline

생성물 1

HCID 212176981-ethyl-4-chloro-6-(methylsulfinyl)-1H-pyrazolo[3,4-b]quinoline수율 93.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

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온도
0 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-3e232b56fa0a4bb5a6b18888c6a443b8
출처 데이터셋
uspto-grants-1996_01
특허 번호
US05488055

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