Cl[C:2]1[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=1.Cl.[Br:13][C:14]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:15]=1[O:16][CH:17]1[CH2:20][NH:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1>[Br:13][C:14]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:15]=1[O:16][CH:17]1[CH2:20][N:19]([C:2]2[N:3]=[CH:4][C:5]([C:8]([O:10][CH3:11])=[O:9])=[N:6][CH:7]=2)[CH2:18]1To a mixture of methyl 5-chloropyrazine-2-carboxylate (0.47 g, 2.7 mmol), 3-(2-bromo-5-fluorophenoxy)azetidine hydrochloride salt (0.80 g, 3.2 mmol) and potassium carbonate (0.75 g, 5.42 mmol) in dioxane (13 mL) was heated at 100° C. After a period of 4 h, the reaction mixture was partitioned between ethyl acetate and saturated ammonium chloride. The organic phase was separated, dried over sodium sulfate, filtered and evaporated under reduced pressure. The resulting solid was taken in ether and filtered to give the title compound.
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