Potassium Carbonate → 3-(1-cyanocyclopropyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide

HRID 1800422노트

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HRID 1800422 반응식
[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([OH:20])[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].Cl[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[C:1]([C:3]1([C:6]2[CH:7]=[C:8]([CH:21]=[CH:22][CH:23]=2)[C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][N:26]=3)[CH:13]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2]

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 673114233-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide

생성물 1

HCID 684192063-(1-cyanocyclopropyl)-N-{4-methoxy-3-[(5-nitropyridin-2-yl)oxy]phenyl}benzamide수율 99%

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of 3-(1-cyanocyclopropyl)-N-(3-hydroxy-4-methoxyphenyl)benzamide (3.11 g, 10.1 mmol) and 2-chloro-5-nitropyridine (1.60 g, 10.1 mmol) in N,N-dimethylformamide (150 mL) was added potassium carbonate (4.24 g, 30.7 mmol), and the mixture was stirred at 60° C. for 16 hr. The reaction solution was cooled to room temperature, and diluted with a mixed solvent (250 mL) of ethyl acetate and hexane (1:1). The solution was washed with water (200 mL×3), and the combined m aqueous layer was extracted with a mixed solvent (100 mL×3) of ethyl acetate and hexane (1:1). The combined organic layer was washed with saturated brine (100 mL), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (4.3 g, 99%) as pale-yellow crystals.

후처리

  1. temperatureThe reaction solution was cooled to room temperature
  2. washThe solution was washed with water (200 mL×3)
  3. extractionthe combined m aqueous layer was extracted with a mixed solvent (100 mL×3) of ethyl acetate and hexane (1:1)
  4. washThe combined organic layer was washed with saturated brine (100 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a9ec3eea055746dd9079826875978ee8
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08344135B2

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