The icons on the pad are telling you that it needs to talk to I tunes before it will work. And you are having trouble making that work. ( is this a new pad, or have you been using it for a while?)
Make sure the I tunes version on your computer is current. If you are not sure, simply fire it up and check for updates. If it still does not recognize the pad, reboot the pad and reboot the computer.
you might want to try a different USB port on your computer.