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

HRID 1269633Notes

Reaction equation

HRID 1269633 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+].[CH3:15][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]([CH3:15])=[CH:17][CH:18]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 79799Tolylboronic acid

Product 1

HCID 184483262-Chloro-6-(4-methylphenyl)pyrazineYield 56.2%

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 (5.55 g, 52 mmol) and 4-methylphenylboronic acid (2.74 g 20 mmol) in dimethoxyethane (90 mL) and water (45 mL) under nitrogen was added tetrakis(triphenylphosphine) palladium (0) (0.46 g). The resulting mixture was heated at reflux for 18 h under nitrogen. After cooling to room temperature, the reaction was diluted with water (100 mL) and extracted with chloroform (2×150 mL). The organic solution was dried MgSO4 and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) 9:1 cyclohexane:EtOAc afforded the title compound as a white solid (2.3 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 18 h under nitrogen
  3. extractionextracted with chloroform (2×150 mL)
  4. customthe solvents removed in vacuo
  5. customPurification by Biotage™ chromatography (Silica, 90 g) 9:1 cyclohexane

Sources & evidence

ORD record
ord-5d209bc6d5b64d99bc535ee090b022a3
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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