Citric Acid → 2-(5-Methoxy-pyridin-2-yl)-benzoic acid diethylamide

HRID 1799030

반응식

HRID 1799030 반응식
P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][N:11]=1.[CH2:18]([N:20]([CH2:32][CH3:33])[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1B(O)O)=[O:22])[CH3:19].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH2:32]([N:20]([CH2:18][CH3:19])[C:21](=[O:22])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][N:11]=1)[CH3:33]

참가 물질

8

반응물 4

HCID 311Citric AcidHCID 62657Potassium Phosphate, TribasicHCID 4190636(2-(Diethylcarbamoyl)phenyl)boronic acidHCID 151690002-Chloro-5-methoxypyridine

생성물 1

HCID 594927872-(5-Methoxy-pyridin-2-yl)-benzoic acid diethylamide수율 28.2%

시약·촉매·용매 3

HCID 962Water용매2회HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
80 °C

실험 절차

Under an argon atmosphere, a mixture of tripotassium phosphate (6.24 g) and water (15 ml) was added to a mixture of 2-chloro-5-methoxy-pyridine (2.05 g), 2-(diethylcarbamoyl)benzeneboronic acid (4.65 g), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride-dichloromethane complex (0.584 g) and toluene (30 ml), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled to room temperature, water (20 ml), citric acid (2.2 g) and ethyl acetate were added and the mixture was stirred and filtered through celite. The filtrate was partitioned in a separatory funnel. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/2) to give a roughly purified product (1.144 g) of the title compound. This product was directly used for the next reaction without further purification.

후처리

  1. temperatureThe reaction mixture was cooled to room temperature
  2. stirringthe mixture was stirred
  3. filtrationfiltered through celite
  4. customThe filtrate was partitioned in a separatory funnel
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customthe obtained residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/1 to 1/2)

출처 및 근거

ORD 기록
ord-0527d7d5ce194bfeb75cd4f1d4458a62
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343994B2

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