A copper-catalysed intramolecular N-arylation of 5-aminopyrazoles is demonstrated for the first time. Highly substituted pyrazolo[3,4-b]indoles are synthesized. In particular, the indole core is decorated with halogens and alkyl and methoxy groups. Furthermore, a selective N-arylation of unsymmetrical diaryl bromide containing pyrazoles is exemplified, resulting in valuable pyrazolo[1,5-a]benzimidazoles.