For my kids, the staying awake at night is almost always overtired. If it were me, I wouldn't wake him to eat. Start his cluster feeds earlier, maybe 5 and 7 and then dreamfeed him before you would expect him to be really hungry so that he's in a deeper sleep when you do it and doesn't wake up. Do you have a good bedtime routine with him yet? If not, this is a good thing to get started too. Finally, don't change his diaper or burp him or anything at his DF if you're having trouble with him waking.