反应详情

温度

100 °C

To a solution of N-(3-bromo-5-nitrophenyl)acetamide of Example 1(c) (5 g, 19.23 mmol) in 1,2-dimethoxyethane (200 ml) were added 4,4,5,5-tetramethyl-2-(5-methylfuran-2-yl)-1,3,2-dioxaborolane (5.9 g, 28.85 mmol), sodium carbonate (8.15 g, 76.92 mmol) and water (20 ml) and the mixture was degassed by N2 bubbling 15 min. Pd(dppf)Cl2 (3.2 g, 3.846 mmol) was added and the mixture was heated at 100° C. for 2 h. The mixture was brought to RT and quenched and extracted as in Example 1(d). The solvent was distilled off and the residue was purified by flash column chromatography (40% ethyl acetate in hexanes) to afford the product in 80% yield (4.0 g). 1H NMR (300 MHz, DMSO-d6): δ 10.45 (s, 1H), 8.4 (s, 1H), 8.2 (d, 2H), 7.1 (s, 1H), 6.2 (s, 1H), 2.4 (s, 3H), 2.15 (s, 3H), Calculated mass: 260.25; Observed mass: 259.1 [M+H]+ (rt: 1.578 min).

1. customthe mixture was degassed by N2 bubbling 15 min
2. customwas brought to RT
3. customquenched
4. extractionextracted as in Example 1(d)
5. distillationThe solvent was distilled off
6. customthe residue was purified by flash column chromatography (40% ethyl acetate in hexanes)
7. customto afford the product in 80% yield (4.0 g)
8. custom259.1 [M+H]+ (rt: 1.578 min)