Yes, such thing is possible using the IP SLA feature. Basically, you perform a test of rechability of the next hop using ordinary pings. If these pings fail, the route will be declared unusable even though the egress interface appears to be alive. That will allow the dynamic route to enter the routing table.
Assume that you are configuring this for a static route towards 10.0.0.0/8 and the next hop is 192.0.2.2 on your Fa0/0 interface. The complete setup would be:
ip sla 1 ! The IP SLA operation is defined here
frequency 10 ! The 192.0.2.2 is pinged each 10 seconds
threshold 500 ! Pings over 500msec are considered delayed
timeout 1000 ! Pings over 1000msec are considered timeouted
ip sla schedule 1 start-time now life forever ! The SLA operation is scheduled to run indefinitely
track 1 rtr 1 reachability ! Track object 1 will hold the result of the IP SLA 1 operation
ip route 192.0.2.2 255.255.255.255 FastEthernet0/0
ip route 192.0.2.2 255.255.255.255 Null0 2
! The previous two lines make sure that the 192.0.2.2 is either reached via Fa0/0 or is never reached
! This is to prevent successfully pinging 192.0.2.2 via some detour
ip route 10.0.0.0 255.255.255.0 192.0.2.2 track 1
Change the IP's accordingly to your setup.
Note: Make sure your IOS supports IP-sla, I guess advance service pack has this feature than other lan-base or any.
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