Compound 6
5-(furan-2-yl)-2-methoxyaniline
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.
To a vial containig a stir bar and 131.4 mg of 5 (0.6 mmol) in 2 mL THF was added 686 µL glacial acetic acid (12 mmol). The solution was stirred at 0°C for 5 min and 1.178 g of powdered zinc (18 mmol) was added. The reaction was allowed to warm to room temperature over 1h. The reaction was then diluted with MeOH, filtered, and concentrated in vacuo. The resulting residue was extracted from saturated sodium bicarbonate with 3 portions of dichloromethane. The pooled organic layer was dried with anhydrous sodium sulfate, filtered, and concentrated to give 94.4 mg (83%) of 6 as an off white solid. MS (ES+) m/z 190.6 (M + H)+1; 1H NMR (DMSO-d6, 400 MHz) δ 3.79 (s, 3H), 4.82 (s, 2H), 6.51 (dd, 1H, J= 3.3, 1.8 Hz), 6.6 (dd, 1H, J=3.3, 0.7 Hz), 6.83 (d, 1H, J=8.5 Hz), 6.9 (dd, 1H, J=8.3, 2.1 Hz), 6.99 (d, 1H, J=2.07 Hz), 7.63 (dd, 1H, 1.7, 0.7 Hz); 13C NMR (DMSO-d6, 400 MHz) δ 55.82, 103.8, 109.44, 111.17, 112.22, 112.42, 123.95, 138.32, 142.08, 146.58, 154.45.
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316894709
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