The structure of the title compound, C27H29N5O4S, displays an intramolecular N—H...O hydrogen bond. The pyrrolo[2,3-b]pyridine core makes a dihedral angle of 85.5 (4)° with the benzyl residue and a dihedral angle of 89.4 (9)° with the tosyl ring. The nitro group is slightly twisted out of the plane of the planar pyrrolopyridine system [(—N—)C—C—N—O torsion angle = −4.61 (18)° and (—NH—)C—C—N—O = −6.46 (18)°]