How do I set up a transfer of money from a traditional IRA to my brokerage account?

It's a little tricky, because what you need to accomplish requires both a transfer of funds and a categorization of the amount. Normally a transfer has no category, because moving funds is neither income nor expense. There is a way to make a transfer have a category, but I don't recommend it because it is something the developers have said they are going to prevent in the future because it's not proper accounting.

Please read this post I recently wrote about how you can accomplish what you need. And while you're there, add your vote for the feature request to add a way to do this more easily in Quicken Mac. (Under the first post in the thread, click on the little arrow in the yellow box.)