Potassium Carbonate → 4-(3-Chloropyrazin-2-yloxy)-N-methoxy-N-methylbenzamide

Reaction equation

[OH:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][CH:3]=1.[Cl:14][C:15]1[C:20](Cl)=[N:19][CH:18]=[CH:17][N:16]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:14][C:15]1[C:20]([O:1][C:2]2[CH:13]=[CH:12][C:5]([C:6]([N:8]([O:10][CH3:11])[CH3:9])=[O:7])=[CH:4][CH:3]=2)=[N:19][CH:18]=[CH:17][N:16]=1

Participants

Procedure

A mixture of 4-hydroxy-N-methoxy-N-methylbenzamide (6.50 g, 35.9 mmol), 2,3-dichloropyrazine (6.95 g, 46.6 mmol), and potassium carbonate (12.40 g, 90 mmol) in acetonitrile (70 mL) was heated at reflux in 18 h. The reaction mixture was cooled, concentrated, taken up in H2O, extracted with EtOAc, dried over MgSO4, concentrated and purified by ISCO (50% EtOAc/Hexanes) to give the titled compound. MS [M+1]: 294.1.