When I try to sync my PDF's it gets stuck, what can I do?

Hi! I tried to sync some of my PDF's into my ipad but when I click 'sync' it appears the 'getting ready to copy' message (step 4 of 4) and gets stuck forever on that step. The PDF's "appear" on ibooks but I can't open it and I've been trying a few times already without getting anywhere.
Anyone has any idea what could be happening? Thank You

What file?

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