Sodium Carbonate → 2-Chloro-6-(4-chlorophenyl)pyrazine

HRID 1269655Notes

Reaction equation

HRID 1269655 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1>C(COC)OC.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>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 785042,6-Dichloropyrazine

Product 1

HCID 214131582-Chloro-6-(4-chlorophenyl)pyrazineYield 308.1%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolvent2×HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 2,6-dichloropyrazine (3 g, 20 mmol), sodium carbonate (5.5 g, 52 mmol) and 4-chlorophenylboronic acid (3.79 g, 3.36 mmol) in dimethoxyethane (140 mL) and water (70 mL) under nitrogen was added tetrakis(triphenylphosphine) palladium (0) (0.46 g). The resulting mixture was heated at reflux for 18 h under nitrogen. The reaction mixture was allowed to cool to room temperature and diluted with water (150 mL) and extracted with dichloromethane (2×200 mL). The organic solution was passed through a hydrophobic frit and the solvents removed in vacuo. Purification by Biotage™ (Si, 90 g) 9:1 cyclohexane:EtOAc afforded the title compound as a white solid (2.33 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 18 h under nitrogen
  3. extractionextracted with dichloromethane (2×200 mL)
  4. customthe solvents removed in vacuo
  5. customPurification by Biotage™ (Si, 90 g) 9:1 cyclohexane

Sources & evidence

ORD record
ord-a39cb0076a2e44beb19ca5f8c0d60875
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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