[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:16]Br>C(O)(=O)C>[CH2:1]([O:8][C:9]1[C:14]([Br:16])=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1A flask was charged with 4-(benzyloxy)pyridin-2-amine (10.69 g, 53.39 mmol) and 20 mL acetic acid was added. Bromine (2.735 ml, 53.39 mmol) and the reaction was stirred for 10 minutes. The reaction mixture was concentrated and purified using silica gel column chromatography eluting with 50%-100% ethyl acetate/hexane provide the desired product (7.0 g, 42.28% yield) as brown solid
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