[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:15][C:16]1[C:21](Cl)=[N:20][CH:19]=[CH:18][N:17]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[Cl:15][C:16]1[C:21]([O:14][C:11]2[CH:12]=[CH:13][C:8]([NH:7][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:9][CH:10]=2)=[N:20][CH:19]=[CH:18][N:17]=1To a solution of 4-(pyridin-2-ylamino)phenol (14.551 g, 78.14 mmol) and 2,3-dichloropyrazine (11.64 g, 78.14 mmol) in DMSO was added CESIUM CARBONATE (30.55 g, 93.77 mmol). The resulting mixture was heated to 60° C. overnight. Aqueous workup was carried out with DCM extraction and washing with alternating water and brine solutions. Purification by Biotage (0-2%, then 2% MeOH/DCM), followed by washing with EtOAc, produced clean product as solid. MS (ESI, pos. ion) m/z: 298.8 (M+1). IC50 (uM) 0.475.
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