Water → ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-{[4-(trifluoromethoxy)benzyl]oxy}-5-pyrimidinecarboxylate

HRID 7418

反応式

HRID 7418 の反応式
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14]2)[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[F:28][C:29]([F:40])([F:39])[O:30][C:31]1[CH:38]=[CH:37][C:34]([CH2:35][OH:36])=[CH:33][CH:32]=1.O>CN(C)C=O>[N:13]1([C:4]2[N:3]=[C:2]([O:36][CH2:35][C:34]3[CH:37]=[CH:38][C:31]([O:30][C:29]([F:28])([F:39])[F:40])=[CH:32][CH:33]=3)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=2)[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14]1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1371844-(Trifluoromethoxy)benzenemethanolHCID 21990788ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate

生成物 1

HCID 21990327ethyl 2-(2,3-dihydro-1H-indol-1-yl)-4-{[4-(trifluoromethoxy)benzyl]oxy}-5-pyrimidinecarboxylate収率 53.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of ethyl 4-chloro-2-(2,3-dihydro-1H-indol-1-yl)-5-pyrimidinecarboxylate (520 mg, 1.72 mmol) in N,N-dimethylformamide (5 mL) was added potassium carbonate (829 mg, 6 mmol) and 4-(trifluoromethoxy)benzyl alcohol (384 mg, 2 mmol) and the mixture was stirred at 100° C. for 18 h. The reaction mixture was allowed to cool to room temperature and water was added, which was followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure and the residue was applied to silica gel column chromatography and eluted with hexane-ethyl acetate (4:1) to give the title compound (420 mg, 53%).

後処理

  1. temperatureto cool to room temperature
  2. extractionwhich was followed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationThe solvent was concentrated under reduced pressure
  6. washeluted with hexane-ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-47cbd00618f04a099dd5260bd5b784b4
出典データセット
uspto-grants-2006_08
特許番号
US07087597B1

関連ノート

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