Toluene → 3-{[4-(1-Methylethyl)phenoxy]methyl}pyridin-2-amine

HRID 1405708노트

반응식

HRID 1405708 반응식
CC(C)([O-])C.[Na+].C1(C(C2C=CC=CC=2)=[NH:14])C=CC=CC=1.Cl[C:22]1[C:27]([CH2:28][O:29][C:30]2[CH:35]=[CH:34][C:33]([CH:36]([CH3:38])[CH3:37])=[CH:32][CH:31]=2)=[CH:26][CH:25]=[CH:24][N:23]=1.C1(C)C=CC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1COCC1>[CH3:37][CH:36]([C:33]1[CH:34]=[CH:35][C:30]([O:29][CH2:28][C:27]2[C:22]([NH2:14])=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:31][CH:32]=1)[CH3:38]

참가 물질

8

반응물 4

HCID 1140TolueneHCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 624715482-Chloro-3-{[4-(1-methylethyl)phenoxy]methyl}pyridine

생성물 1

HCID 150356783-{[4-(1-Methylethyl)phenoxy]methyl}pyridin-2-amine수율 87%

시약·촉매·용매 3

HCID 634876Binap, (A+-)-촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

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온도
110 °C

실험 절차

A mixture of sodium tert-butoxide (0.617 g), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.160 g), 1,1-diphenylmethanimine (1.008 g), 2-chloro-3-{[4-(1-methylethyl)phenoxy]methyl}pyridine (1.12 g), tris(dibenzylideneacetone)dipalladium(0) (0.118 g) and toluene (20 mL) was stirred at 110° C. for 6 hr. To the reaction mixture was added THF, and the mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. To the residue were added THF (25 mL) and 1M hydrochloric acid (25 mL) at room temperature, and the mixture was stirred overnight. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate/hexane) to give the title compound (902.2 mg) containing impurity as a pale-yellow oil.

후처리

  1. filtrationthe mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue were added THF (25 mL) and 1M hydrochloric acid (25 mL) at room temperature
  4. stirringthe mixture was stirred overnight
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by basic silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f253e5b45b894ea39c2bdb630c417440
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08916551B2

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