2-Bromopyridine → 2-(3-Vinylphenyl)pyridine

HRID 431840Notes

Reaction equation

HRID 431840 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)=[CH2:2].Br[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>[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.O1CCCC1>[CH:1]([C:3]1[CH:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[CH:6]=[CH:7][CH:8]=1)=[CH2:2]

Participants

6

Reactant 3

HCID 79732-BromopyridineHCID 11430Potassium CarbonateHCID 43668863-Vinylphenylboronic Acid (contains varying amounts of Anhydride)

Product 1

HCID 187617062-(3-Vinylphenyl)pyridineYield 80%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The reaction was performed with 3-vinyl-phenylboronic acid (10 g, 0.0676 mol), 2-bromopyridine (12.64 g, 0.08 mol), tetrahydrofuran (100 ml), 2M potassium carbonate aqueous solution (26 ml), and tetrakis(triphenylphosphine) palladium (Pd(Ph3)4, 0.06 g, 1 mol %) according to Example 1. The yield was 80%.

Sources & evidence

ORD record
ord-87337c92711549049cd4b74d0c50d7b8
Source dataset
uspto-grants-2003_12
Patent number
US06660821B2

Reaction notes

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