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

HRID 1672235Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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%),

Workup

temperatureto cool to rt
customThe organic solution was separated
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-42e49160b0a546f4be4444a2cd0212d2
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998952B2

Reaction notes

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