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

HRID 1586186노트

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HRID 1586186 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. 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.

후처리

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

출처 및 근거

ORD 기록
ord-98eddf10ab54442bbb3585dbeec25967
출처 데이터셋
uspto-grants-1999_08
특허 번호
US05942520

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