3-Nitrophenylboronic Acid → 2-(3-Nitrophenyl)pyrazine
Reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[CH:4][N:3]=1.[N+:8]([C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1)([O-:10])=[O:9].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.ClCCl.[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>[N+:8]([C:11]1[CH:16]=[C:15]([C:2]2[CH:7]=[N:6][CH:5]=[CH:4][N:3]=2)[CH:14]=[CH:13][CH:12]=1)([O-:10])=[O:9]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
To a suspension of 2-chloropyrazine (1.14 g), 3-nitrophenylboronic acid (2.00 g) and tetrakis(triphenylphosphine)-palladium (346 mg) in 1,2-dimethoxyethane (30 ml) was added an aqueous solution of sodium carbonate (2M, 12 ml) followed by stirring at 80° C. for 18 hours. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with methanol and collected by filtration. The obtained product was washed with methanol and diisopropyl ether and dried to give 2-(3-nitrophenyl)pyrazine (1.78 g, 88.6%).
Workup
- washwashed with water and brine
- dry with materialThe organic layer was dried over magnesium sulfate
- customevaporated under reduced pressure
- customThe residue was triturated with methanol
- filtrationcollected by filtration
- washThe obtained product was washed with methanol and diisopropyl ether
- customdried
Sources & evidence
- ORD record
- ord-8991ca3cc60a42a7b357c59f25b7c6c9
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770667B1
Reaction notes
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