When did you drop to a 1hr nap?

My son is 27 months and lower sleep needs. Definitely still needs a nap, but his bedtime and middle of the night wakes are becoming a problem since he’s dipping into his overnight sleep.

Current schedule is 7am wake 1:45-3pm nap 9:30pm bedtime 😵‍💫

The nap time is based on the earliest when he’d allow us to put him to sleep. He fights otherwise and he’s lower sleep needs. The last schedule that worked was the above but with a 9pm bedtime.

The bedtime used to be 9pm but he’s been fighting hard with excuses and ultimately doesn’t fall asleep until 9:30pm anyways.

I think this schedule is just not working for him at all. It’s just too much awake time, but not sure how to go about fixing it. He’s miserable after an hour nap.