Triethylamine → N-[4-(4-bromophenoxy)benzyl]-N-(2,4-difluorobenzyl)-2-methyl-3-nitroaniline

Participants

Reaction Steps

The product from Example 33A (1.0 g, 2.6 mmoles), 4 Å molecular sieves, Cu(OAc)2 (0.71 g, 3.91 mmoles) and 4-bromophenylboronic acid (1.57 g, 7.81 mmoles) in CH2Cl2 (20 mL) was treated with triethylamine (1.81 mL, 13.0 mmoles) and the resulting solution was stirred vigorously overnight. An additional equivalent of Cu(OAc)2, 4-bromophenylboronic acid, and triethylamine were added and the reaction mixture was stirred vigorously for 5 hours. The mixture was filtered through a 1 inch pad of Celite using CH2Cl2 and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, 10:1 hexanes:ethyl acetate) to provide the title compound as a yellow oil (0.87 g, 62%).

Provenance & Evidence