[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[NH2:8].CCN(C(C)C)C(C)C.[C:18](Cl)(Cl)=[O:19].[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]([OH:31])[CH3:30]>C1(C)C=CC=CC=1.CCOC(C)=O.O>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[CH:29]([O:31][C:18](=[O:19])[NH:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[Br:1])[CH3:30]3-Bromo-pyridin-4-ylamine (0.55 g, 3.2 mmol) was dissolved in toluene (2 mL) then Hünig's base (1.1 mL, 6.4 mmol) and phosgene (1.9M in toluene, 1.8 mL, 3.5 mmol) were added. 1-(2-Chloro-phenyl)-ethanol (0.5 g, 3.2 mmol) in toluene (3 mL) was added and the reaction was heated to 100° C. for 2.5 hours, when no starting material remained by analytical LCMS. The reaction was submitted to EtOAc/H2O workup then purified via silica gel chromatography to provide the title compound.
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