2,6-Dichloropyrazine → 2-Chloro-6-(4-fluorophenyl)pyrazine(WXFC0484)

HRID 539628Notes

Reaction equation

HRID 539628 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[F:9][C:10]1[CH:15]=[CH:14][C:13](B(O)O)=[CH:12][CH:11]=1>O1CCOCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:13]2[CH:14]=[CH:15][C:10]([F:9])=[CH:11][CH:12]=2)[N:3]=1

Participants

4

Reactant 2

HCID 785042,6-DichloropyrazineHCID 2856454-Fluorophenylboronic acid

Product 1

HCID 545956102-Chloro-6-(4-fluorophenyl)pyrazine(WXFC0484)Yield 34.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 2,6-dichloropyrazine (2.75 g, 18.3 mmol), 4-fluorophenyl boronic acid (2.3 g, 16.5 mmol) and palladium tetrakis triphenylphosphine (0.1 g) in dioxane (50 mL) was stirred at 60° C. for one hour. The mixture was cooled and partitioned between water and diethyl ether. The organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was recrystallized from diethyl ether and methanol to give 1.2 g of 2-chloro-6-(4-fluoro-phenyl)-pyrazine.

Workup

  1. temperatureThe mixture was cooled
  2. custompartitioned between water and diethyl ether
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was recrystallized from diethyl ether and methanol

Sources & evidence

ORD record
ord-1ac7e4c608414598afaeee6cb842f96b
Source dataset
uspto-grants-2014_10
Patent number
US08871760B2

Reaction notes

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