Unfortunately you can't use CoreAnimation to do this (which would make it rather easy).
Looking at Apple's CoreAnimation documentation:
iOS Note: As a performance consideration, iOS does not support the mask property.
Therefore the next best way to do this is to use Quartz 2D (as answered here):
CGContextRef mainViewContentContext;
CGColorSpaceRef colorSpace;
colorSpace = CGColorSpaceCreateDeviceRGB();
// create a bitmap graphics context the size of the image
mainViewContentContext = CGBitmapContextCreate (NULL, targetSize.width, targetSize.height, 8, 0, colorSpace, kCGImageAlphaPremultipliedLast);
// free the rgb colorspace
CGColorSpaceRelease(colorSpace);
if (mainViewContentContext==NULL)
return NULL;
CGImageRef maskImage = [[UIImage imageNamed:@"mask.png"] CGImage];
CGContextClipToMask(mainViewContentContext, CGRectMake(0, 0, targetSize.width, targetSize.height), maskImage);
CGContextDrawImage(mainViewContentContext, CGRectMake(thumbnailPoint.x, thumbnailPoint.y, scaledWidth, scaledHeight), self.CGImage);
// Create CGImageRef of the main view bitmap content, and then
// release that bitmap context
CGImageRef mainViewContentBitmapContext = CGBitmapContextCreateImage(mainViewContentContext);
CGContextRelease(mainViewContentContext);
// convert the finished resized image to a UIImage
UIImage *theImage = [UIImage imageWithCGImage:mainViewContentBitmapContext];
// image is retained by the property setting above, so we can
// release the original
CGImageRelease(mainViewContentBitmapContext);
// return the image
return theImage;