The tapered holes were probably cut by a tapered reamer after first drilling a pilot hole. (Colt holds the sight base in alignment on the barrel, drills through from one side, then runs a tapered reamer through from the other.) I do not know of a source for the reamer and even still you would have the problem of cutting the barrel notch without enlarging the sight base holes. Here is one way tou could do it:
Pin the sight on with the rear pin. Working through the front hole, use a miniature round file to begin cutting the new notch. Once the notch is accurately located, remove the sight and finish with a file the same diameter as the pin. The original front notch is what you are trying to duplicate, so you can use it as a reference. Work slowly. When the pin fits in to it's original depth you are done. As you approach the final depth, you can use a marking pen to coat the cut surface. Drive the pin in (with the rear pin already in), And it will wipe off the marker from whatever high spot still needs work.
Just a note: Standard round (rat-tail) files are tapered. Chain saw files are straight.