Potassium Carbonate → 1'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-one

HRID 2036118ノート

反応式

HRID 2036118 の反応式
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[N:9]=2)=[CH:6][CH:7]=1.[NH:14]1[CH2:18][CH2:17][C:16]2([C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:27])[CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:13][C:10]1[N:9]=[C:8]([C:5]2[N:4]=[N:3][C:2]([N:14]3[CH2:18][CH2:17][C:16]4([C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[NH:20][C:19]4=[O:27])[CH2:15]3)=[CH:7][CH:6]=2)[O:12][N:11]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 10954296Spiro[3H-indole-3,3'-pyrrolidin]-2(1H)-oneHCID 167322943-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine

生成物 1

HCID 685546001'-[6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazin-3-yl]spiro[indole-3,3'-pyrrolidin]-2(1H)-one収率 62%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 8857Ethyl Acetate溶媒HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

3-Chloro-6-(3-methyl-1,2,4-oxadiazol-5-yl)pyridazine (690 mg) obtained in Example 43(2), spiro[indole-3,3′-pyrrolidin]-2(1H)-one (800 mg), potassium carbonate (500 mg) and tetrabutylammonium iodide (130 mg) were suspended in N,N-dimethylformamide-tetrahydrofuran (1:1, v/v, 50 mL), and the suspension was stirred at 120° C. overnight. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with aqueous sodium carbonate solution. The organic layer was dried over sodium sulfate and the solvent was evaporated under reduced pressure. Ethyl acetate was added and the resulting precipitate was collected by filtration, and recrystallized from ethyl acetate to give the object product (750 mg, 62%).

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. washwashed with aqueous sodium carbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionEthyl acetate was added
  6. filtrationthe resulting precipitate was collected by filtration
  7. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-8b967e958ac5430e88063481c8156955
出典データセット
uspto-grants-2013_11
特許番号
US08575167B2

反応ノート

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