I have a problem with a mitsunobu reaction.
I'm trying to make the ether of 2-amino-4-hydroxyquinoline with N-Boc-ethanolamine.
I have mixed 2-amino-4-hydroxyquinoline, PPh3 and ethanolamine to freshly distilled THF (2 mL, 0.3M solution of quinoline). After cooling to 0°C I added DIAD under argon. The suspension (the quinoline seems to be insoluble in THF) was stirred for 3days, but I cannot find any trace of products, analysis was made by reverse phase LC-MS.