I didn't know there were special compilers for noobs.
I am currently using the open-source IDE "Integrated Development Environment" called Code::Blocks, which comes bundled with a fairly fresh GCC compiler. It's free and easy to set up.
I would set your brother up with mingw and notepad++.
It might take a little more work to get things installed and working properly, but having the only output be to console makes it simpler to figure out what is going wrong with code.
We use Visual Studio/Linux in my university.
But I heard codeblocks is good too. With notepad++ i think you need some sort of external launcher to run a program, not sure though.