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

HRID 2388026노트

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HRID 2388026 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-3e05e4ed91d640f6b97f54a238301d69
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268992B2

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