No you cannot force a file that is already committed in the repo to be removed just because it is added to the .gitignore
You have to git rm --cached to remove the files that you don't want in the repo. ( --cached since you probably want to keep the local copy but remove from the repo. ) So if you want to remove all the exe's from your repo do
git rm --cached /*.exe
(Note that the asterisk * is quoted from the shell - this lets git, and not the shell, expand the pathnames of files and subdirectories)
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