Potassium Carbonate → Methyl 2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate

HRID 2389874노트

반응식

HRID 2389874 반응식
[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][CH2:22][CH2:23][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[CH2:23][CH2:22][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

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 138378Phenylpropynoic acid methyl esterHCID 866386665-Amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate

생성물 1

HCID 53310988Methyl 2-phenyl-8,9-dihydrofuro[3,2-c]pyrazolo[1,5-a]pyridine-1-carboxylate수율 18.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 5-amino-2,3-dihydrofuro[3,2-c]pyridin-5-ium 2,4-dinitrobenzenolate (1.00 g, 3.12 mmol) and potassium carbonate (640 mg, 4.37 mmol) in dimethylformamide (20 mL) was added methyl 3-phenylpropiolate (506 μL, 3.43 mmol) under ice-cooling, and the mixture was stirred at room temperature for 14 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=30/70→40/60) to give the title compound (166 mg, yield 18%).

후처리

  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=30/70→40/60)

출처 및 근거

ORD 기록
ord-acfa1e7e0a054766b56f573b43e0a6ae
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273761B2

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