Cuminol → 3-{[4-(1-Methylethyl)benzyl]oxy}pyridin-2-amine

HRID 1622630노트

반응식

HRID 1622630 반응식
C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[CH:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][OH:31])=[CH:26][CH:25]=1)([CH3:23])[CH3:22].Br[C:33]1[C:34]([NH2:39])=[N:35][CH:36]=[CH:37][CH:38]=1>C1(C)C=CC=CC=1.[Cl-].[Na+].O.[Cu]I>[CH3:22][CH:21]([C:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:33]2[C:34]([NH2:39])=[N:35][CH:36]=[CH:37][CH:38]=2)=[CH:26][CH:25]=1)[CH3:23]

참가 물질

8

반응물 4

HCID 325CuminolHCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 8177002-Amino-3-bromopyridine

생성물 1

HCID 289817923-{[4-(1-Methylethyl)benzyl]oxy}pyridin-2-amine수율 65.7%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 1140Toluene용매HCID 57417360Sodium chloride; water용매

반응 조건

온도
110 °C

실험 절차

A mixture of cesium carbonate (2.82 g), 1,10-phenanthrolin (0.208 g), (4-isopropylphenyl)methanol (8.68 g), 3-bromopyridin-2-amine (1 g) and copper (I) iodide (0.110 g) in toluene (10 mL) was stirred under a nitrogen atmosphere at 110° C. overnight, and at 130° C. for 5 hr. The reaction mixture was added to saturated brine, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.92 g) as a pale-yellow solid.

후처리

  1. waitat 130° C. for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-5e8eed1685c94255a5f18d2a8f3b9a8e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778934B2

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