A practical and efficient synthesis of 4-amino-7-bromoimidazo [2,1-f][1,2,4]triazine 1  was described. In the presence of potassium tert-butoxide, reaction of O-(4-nitrobenzoyl)hydroxylamine with 1H-?imidazole-?2-?carbonitrile hydrochloride 2   yield aminoimdazole 3  , which reacted with formamidine to provide imidazo[2,?1-?f]?[1,?2,?4]?triazin-?4-?amine 4 in high yield  . The following bromination of 4 afforded the title compound 1 in near quantatitive yield  . This new protocol was successfully applied to kilo scale production of compound 1   via three steps with 53% overall yield (Fig. 1  ).

Process development of 4-amino-7-bromoimidazo[2,1-f][1,2,4]triazine

248th National Meeting (2014)

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