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

HRID 541149

反応式

HRID 541149 の反応式
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]

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-996e065bbc964b5c82d86c73e3dba0a9
出典データセット
uspto-grants-2014_10
特許番号
US08871934B2

関連ノート

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