Methyl 4-bromobenzoate → Methyl 4-(4-(((2,4-difluorobenzyl)(2-methyl-3-nitrophenyl)amino)methyl)phenoxy)benzoate

Participants

Reaction Conditions

Reaction Steps

The product from Example 33A (0.1520 g, 0.396 mmoles), methyl-4-bromobenzoate (0.1702 g, 0.792 mmoles), K3PO4 (0.1680 g, 0.792 mmoles), Pd(OAc)2 (0.0070 g, 0.032 mmoles), and 2-(di-tert-butylphosphino)biphenyl (0.0140 g, 0.048 mmoles) was treated with toluene (1.16 mL) under a nitrogen atmosphere. The resulting red solution was degassed, stirred for 10 min, and heated to 100° C. overnight. The black solution was diluted with diethyl ether, extracted with sat. NH4Cl and sat. NaCl, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by flash chromatography (10:1 hexane:ethyl acetate) on silica gel to provide the title compound (0.1886 g, 92%) as a yellow oil.

Provenance & Evidence