Abstract:The nitro group of methyl 3-nitropyridine-4-carboxylate (1) has successfully been replaced by fluoride anion via nucleophilic aromatic substitution to give the 3-fluoropyridine-4-carboxylate 2.
The preparation of oxazolo[4,5-c]pyridine and 6-azaindole from 4-bromo-3-pivaloylaminopyridine (8) is reported. The oxazolopyridine 2-tert-butyl-oxazolo[4,5-c]pyridine (9) was successfully prepared from 8 in 78% yield by a new base/TBAB promoted non-catalyzed microwave cyclisation strategy (10 min) or, alternatively, in 54% yield by conventional heating (48 hrs) and CuI catalysis. The 6-azaindole 2-phenyl-1-(trimethylacetyl)-6-azaindole (13) was prepared from 8 in a two step procedure, including a Sonogashira coupling reaction.
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