Nitrogen → N-(2',5'-difluoro-5-nitrobiphenyl-3-yl)acetamide

Participants

Reaction Steps

A solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (0.8 g, 3.07 mmol) in 1,2-dimethoxyethane (15 ml) was degassed by N2 bubbling for 5 min. 2,5-Difluorophenylboronic acid (0.58 g, 3.69 mmol, 1.2 eq.) was added and the mixture was degassed for another 5 min. Pd(dppf)Cl2 (0.5 g, 0.615 mmol, 0.2 eq.) and aqueous sodium carbonate (0.98 g, 9.23 mmol, 3.0 eq.) were added and the procedure of Example 1(d) was followed. The crude residue of the product was purified by column chromatography (60-120 silica gel, 25% ethyl acetate in hexane) to give the product in 67% yield (0.6 g). 1H NMR (300 MHz, DMSO-d6): δ 10.56 (s, 1H), 8.65 (t, 1H), 8.14 (s, 1H), 8.06 (s, 1H), 7.56-7.52 (m, 1H), 7.47-7.37 (m, 2H), 2.12 (s, 3H).

Provenance & Evidence