Water → 3-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,6'-trimethyl-[2,2']bipyridine

HRID 229067

반응식

HRID 229067 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([OH:16])[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=2)=[N:6][C:7]=1[CH3:8].[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29](Cl)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C1C=CN=CC=1.CS(C)=O>[CH2:17]([O:24][C:25]1[CH:34]=[C:33]2[C:28]([C:29]([O:16][C:4]3[C:5]([C:9]4[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=4)=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)=[CH:30][CH:31]=[N:32]2)=[CH:27][C:26]=1[O:36][CH3:37])[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 10796Cesium carbonateHCID 226465627-(Benzyloxy)-4-chloro-6-methoxyquinolineHCID 1363851075,6-Dimethyl-2-(6-methylpyridin-2-yl)pyridin-3-ol

생성물 1

HCID 577565403-(7-Benzyloxy-6-methoxy-quinolin-4-yloxy)-5,6,6'-trimethyl-[2,2']bipyridine수율 72.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

5,6,6′-Trimethyl-[2,2′]bipyridin-3-ol (300 mg), 7-benzyloxy-4-chloro-6-methoxyquinoline (1.26 g), 4-dimethylaminopyridine (513 mg), and cesium carbonate (1.37 g) were suspended in dimethyl sulfoxide (6 ml), and the suspension was stirred at 130° C. overnight. The reaction solution was cooled to room temperature, water was then added to the reaction solution, and the mixture was extracted with chloroform. The chloroform layer was washed with saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed by distillation under the reduced pressure, and the residue was purified by column chromatography using chloroform-methanol to give the title compound (483 mg, yield 72%).

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionthe mixture was extracted with chloroform
  3. washThe chloroform layer was washed with saturated brine
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed by distillation under the reduced pressure
  6. customthe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-146fedd606cf4b43b92bd93f65c0f8f9
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560558B2

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