Potassium Carbonate → Methyl 2-phenylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

HRID 2389871ノート

反応式

HRID 2389871 の反応式
[N+](C1C=C([N+]([O-])=O)C=CC=1[O-])([O-])=O.[NH2:14][N+:15]1[CH:20]=[CH:19][C:18]2[O:21][CH:22]=[CH:23][C:17]=2[CH:16]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1([C:36]#[C:37][C:38]([O:40][CH3:41])=[O:39])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C)C=O.O>[C:30]1([C:36]2[C:37]([C:38]([O:40][CH3:41])=[O:39])=[C:16]3[C:17]4[CH:23]=[CH:22][O:21][C:18]=4[CH:19]=[CH:20][N:15]3[N:14]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 138378Phenylpropynoic acid methyl esterHCID 866386655-Aminofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

生成物 1

HCID 59179362Methyl 2-phenylfuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate収率 51%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 5-aminofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (1.00 g, 3.14 mmol) and potassium carbonate (608 mg, 4.40 mmol) in dimethylformamide (20 mL) was added methyl 3-phenylpropiolate (509 μL, 3.45 mmol) under ice-cooling, and the mixture was stirred at room temperature for 15 hr. The reaction solution was diluted with water and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60) to give the title compound (467 mg, yield 51%).

後処理

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→40/60)

出典と根拠

ORDレコード
ord-e50c3208e3c54f509d94441ea5280e46
出典データセット
uspto-grants-2012_09
特許番号
US08273761B2

反応ノート

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