The President has made so-called "recess appointments" to the CFPB and NLRB during a time when the Senate was technically, if not literally, in session. These actions will almost surely go to the Supreme Court, after slogging through the lower courts.
Whether this president will still be in office by the time the Supremes get the case is a good question? Answer: probably not. Will a change of president make the case moot? Again, probably not.