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The N‐functionalization of 4‐amino‐2‐trifluoromethyl‐1H‐pyrroles using alkyl halides is reported. The selectivity of the alkylation reaction was highly dependent on the nature of the alkyl halide and the reaction conditions applied, that is, methyl iodide may furnish N‐methyl or N,N‐dimethyl pyrroles, while allyl bromide furnishes N‐allyl or N,C‐diallyl analogs and propargyl bromide furnishes exclusively...