1,4-Dioxane → (2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone

HRID 526830노트

반응식

HRID 526830 반응식
O1CCOCC1.[Cl:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([Cl:24])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([CH:25]([C:27]3[O:31][N:30]=[C:29]([CH3:32])[CH:28]=3)[OH:26])[CH:14]=2)[N:9]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[Cl:7][C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:16]([Cl:24])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:25]([C:27]3[O:31][N:30]=[C:29]([CH3:32])[CH:28]=3)=[O:26])[CH:14]=2)[N:9]=1

참가 물질

5

반응물 2

HCID 312751,4-DioxaneHCID 86716079(2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanol

생성물 1

HCID 86716078(2,4-Dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanone

시약·촉매·용매 2

HCID 178418406HCID 178418406, 화합물촉매HCID 6344Dichloromethane용매

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온도
100 °C

실험 절차

1,4-dioxane (7.5 mL) and manganese (IV) dioxide (447 mg, 5.14 mmol) were added to crude (2,4-dichloro-3-phenylquinolin-6-yl)(3-methylisoxazol-5-yl)methanol (Intermediate 3: step a, 1.03 mmol assuming theoretical yield in prior step). The resulting black suspension was heated in a 100° C. oil bath in a sealed tube for 3 hours then cooled to room temperature. The mixture was then diluted with DCM, and filtered through Celite®. The filtrate was concentrated and the residue was purified by flash column chromatography (silica gel, 3-15% EtOAc-heptane) to afford slightly impure title compound which was used without further purification.

후처리

  1. customstep a, 1.03 mmol assuming theoretical yield in prior step)
  2. temperaturethen cooled to room temperature
  3. filtrationfiltered through Celite®
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by flash column chromatography (silica gel, 3-15% EtOAc-heptane)

출처 및 근거

ORD 기록
ord-82764dc173ce429faadb8966689d7532
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346782B2

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