FR 5322 then IB 601 at Madrid
Milan → Madrid → Brussels
Timetable, Madrid time
19:45FR 5322 from Milan at the gate
16:25IB 601 to Brussels leaves the gatealso LA 1566, VY 5097, BT 5171, AA 8624
20 h 40 apart on the timetable, overnight
IB 601 leaves 20 h 40 after FR 5322 arrives on the timetable: more than half a day, so not a connection we count.