Are you just looking to verify that the file is of a given extension? You can simplify what you are trying to do with something like this:
(.*?)\.(jpg|gif|doc|pdf)$
Then, when you call IsMatch() make sure to pass RegexOptions.IgnoreCase as your second parameter. There is no reason to have to list out the variations for casing.
Edit: As Dario mentions, this is not going to work for the RegularExpressionValidator, as it does not support casing options.