[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=1.Cl[C:16]1[C:17]([C:22]([O:24][CH3:25])=[O:23])=[N:18][CH:19]=[CH:20][N:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CS(C)=O>O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:16]2[C:17]([C:22]([O:24][CH3:25])=[O:23])=[N:18][CH:19]=[CH:20][N:21]=2)=[CH:10][CH:9]=1
To a 350 mL sealable tubed was added 4-(pyridin-2-ylamino)phenol (5.16 g, 27.7 mmol), methyl 3-chloropyrazine-2-carboxylate (4.78 g, 27.7 mmol), and cesium carbonate (9.93 g, 30.5 mmol) with DMSO. The tube was sealed and heated to 100° C. for three days. After cooling to temperature, the reaction was diluted with water and extracted with ethyl acetate. The combined, dark brown organics were dried over sodium sulfate, filtered, and concentrated in vacuo. The brown residue was adsorbed onto silica under high vacuum and flash purified on (0.5 to 10% MeOH/DCM), affording the product as a pale tan solid (7.44 g, 23.1 mmol, 83%). MS (ESI, pos. ion) m/z: 323.0 (M+1).
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