The broader and systematic application of a novel scaffold is often hampered by the unavailability of a short and reliable synthetic access. We investigated a new strategy for the design and synthesis of an array of N2‐substituted aza‐2H‐indazole derivatives as potential kinase inhibitors. Guided by a rational ligand alignment approach to qualify the so far underrepresented aza‐2H‐indazole scaffold, indazoles were connected in N2‐position with a phenyl spacer and an arylsulfonamide or amide linkage. Initial profiling against a panel of 30 kinases confirmed the in silico predicted selectivity bias. A synthesized focused library of 52 different aza‐2H‐indazole derivatives showed good initial selective inhibition against SGK1, Tie2 and SRC kinase with the best representatives having IC50s in the range of up to 500 nM. In a comparative computational study, these data were analyzed and rationalized in the light of docking studies.