Compound 5
2-(4-methoxy-3-nitrophenyl)furan
From: Overcoming resistance to HER2 inhibitors through state-specific kinase binding
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
5-A vial containing a stir bar and a solution of 166.3mg of 4-bromo-2-nitroanisole (.72 mmol) and 247.6 mg 2-furanylboronic acid MIDA ester (1.11 mmol) in 4.35 mL of 1,2 dimethoxyethane and 2.9 mL of 1M Na2CO3 in H2O was sparged with argon for 5 min. 172 mg of tetrakis(triphenylphosphine)palladium(0) (0.15 mmol) was added and the reaction, which was purged with argon and stirred at 80°C for 12h. The reaction was cooled and water was added to the reaction mixture, which was extracted 3 times with dichloromethane. The combined organic layer was washed with brine, dried with anhydrous sodium sulfate, filtered and concentrated by rotary evaporation. The residue was purified by silica gel chromatography (eluent, Hex:EtOAc = 1:0 to 3:1) to give 140.4 mg (89%) of 5 as a yellow solid. MS (ES+) m/z 220.4 (M + H)+1; 1H NMR (DMSO-d6, 400 MHz) δ 3.96, (s, 3H), 6.62 (dd, 1H, J=3.4, 1.8 Hz). 7.03 (dd, 1H, J=3.4, 0.7 Hz), 7.44 (d, 1H, J=9.1 Hz), 7.77 (dd, 1H, J=1.8, 0.7 Hz), 7.97 (dd, 1H, J=8.8, 2.3 Hz), 8.17 (d, 1H, J=2.3 Hz); 13C NMR (DMSO-d6, 500 MHz) δ 57.31, 106.85, 112.74, 115.50, 120.06, 123.67, 129.43, 140.11, 143.72, 151.28, 151.37.
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