1,2-Dimethoxyethane → 3-bromo-5-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyridine

HRID 1672235노트

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HRID 1672235 반응식
[Br:1][C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][CH:5]=[C:6](Br)[CH:7]=1.[CH2:13]([O:15]/[CH:16]=[CH:17]/B1OC(C)(C)C(C)(C)O1)[CH3:14].COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[C:3]([C:9]([F:12])([F:11])[F:10])=[N:4][CH:5]=[C:6](/[CH:14]=[CH:13]/[O:15][CH2:16][CH3:17])[CH:7]=1

참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 110449423,5-Dibromo-2-(trifluoromethyl)pyridineHCID 219739081-Ethoxyethene-2-boronic acid pinacol ester

생성물 1

HCID 594049863-bromo-5-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyridine수율 38%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

To a solution of 3,5-dibromo-2-(trifluoromethyl)pyridine (1.11 g, 3.65 mmol) in water (9 mL) were added 2-[(E)-2-ethoxyvinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.72 g, 3.65 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.42 g, 0.36 mmol), 1,2-dimethoxyethane (16.7 mL), and sodium carbonate (1.16 g, 11.0 mmol). The resulting mixture was allowed to stir overnight at 60° C. After the reaction was allowed to cool to rt, EtOAc (50 mL) was added. The organic solution was separated, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to give 3-bromo-5-[(E)-2-ethoxyvinyl]-2-(trifluoromethyl)pyridine (0.41 g, 38%),

후처리

  1. temperatureto cool to rt
  2. customThe organic solution was separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-42e49160b0a546f4be4444a2cd0212d2
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998952B2

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