Is path broken for anaconda ipython?

Your problem is in your $PATH. If you look at your traceback, it's running /usr/local/bin/ipython - this is the one that is installed by Homebrew, and not by Anaconda. (Anaconda installs everything into /anaconda/bin.)

The reason this is getting picked up is because the very last line of your .bash_profile sticks /usr/local/bin at the front of your path. This means that the ipython that you installed via Homebrew is masking the one that's installed by Anaconda.

You have two options:

1. Uninstall the ipython that Homebrew installed, and just use Anaconda for your Python packages.

2. In your .bash_profile, move the Homebrew PATH modification line above the Anaconda one. This way, Anaconda's ipython, python, and various other Python commands will take precedence.

Remember, if you change your .bash_profile, you need to close your Terminal and start a new one for the changes to take effect.

It looks like your path is completely ok. Notice that the error comes from "/usr/local/bin/ipython". It is not a bash error, it is more likely an error involving setup_tools, or pip, that is Python packaging tools. Bash finds ipython and executes ipython startup file but encounters an error there.

The error appears to be saying that your version of ipython is incompatible. Have you tried doing something like this?

 conda update conda conda update ipython

Updaing conda and ipython is recommended in iPython documentation. Perhaps this will fix the problem. If not, then add an information saying that you updated conda and ipython to your question.

One possible reason is that there are multiple ipython versions installed e.g., brew might install to /usr/local/bin, conda might install to /anaconda/bin (it is just a guess). The advice from similar issue is to remove all ipython installation completely and install the one that you will use.