Sodium Carbonate → 2-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazine

HRID 1269632Notes

Reaction equation

HRID 1269632 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+].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=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:20]2[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=2)[N:3]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 184483272-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazineYield 36.5%

Reagents, catalysts & solvents 3

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

Procedure

To a mixture of 2,6-dichloropyrazine (0.5 g, 3.36 mmol), sodium carbonate (0.925 g, 8.73 mmol) and 4-trifluoromethylphenylboronic acid (0.638 g, 3.36 mmol) in dimethoxyethane (15 mL) and water (7.5 mL) under nitrogen was added tetrakis(triphenylphosphine) palladium (0) (0.078 g). The resulting mixture was heated at reflux for 5 h under nitrogen, before stirring at room temperature overnight. The reaction was diluted with water (50 mL) and extracted with chloroform (2×75 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) 10:1–6:1 cyclohexane:EtOAc afforded the title compound as a white solid (0.317 g).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 h under nitrogen
  3. extractionextracted with chloroform (2×75 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customPurification by Biotage™ chromatography (Silica, 90 g) 10:1–6:1 cyclohexane

Sources & evidence

ORD record
ord-95d5904f7e594812983978ced455bd3a
Source dataset
uspto-grants-2007_04
Patent number
US07199239B2

Reaction notes

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