[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][N:3]=1.O.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.[C:24](#[N:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>[Cu]Br>[Br:8][C:6]1[CH:5]=[CH:4][N:3]2[N:31]=[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:1]=[C:2]2[CH:7]=1A mixture of 2-amino-4-bromopyridine (1.00 g, 5.66 mmol), copper (I) bromide (41.5 mg, 0.28 mmol), 1,10-phenanthroline monohydrate (56.7 mg, 0.28 mmol) and benzonitrile (13 mL) was heated in a 100-mL 4-necked flask to 110° C. During 23 h a gentle flow of O2/N2 (5:95) was bubbled through the reaction mixture (>99% conversion, HPLC method cf. example 1.1). The dark brown suspension was then cooled to 0-5° C. and filtered. The filter cake was washed with TBME (50 mL) and dried to yield crude 7-bromo-2-phenyl-[1,2,4]triazolo[1,5-a]pyridine (1.21 g, 79%) as a green solid with 99.0% purity (HPLC area-%, HPLC method cf. example 1.1).
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