反应详情

温度

110 °C

A suspension of 175 (500 mg, 2.00 mmol, scheme 35), 416 (406 mg, 2.60 mmol), Pd2(dba)3 (73 mg, 0.08 mmol), (2-biphenyl)dicyclohexylphosphine (56 mg, 0.16 mmol), and K3PO4 (638 mg, 3.00 mmol) in toluene (20 ml) was degassed for 15 min with nitrogen, and then heated at 110° C. for 22 hrs in a sealed flask [ J. P. Wolfe, H. Tomori J. P. Sadighi J. Yin, S. L. Buchwald J. Org. Chem. 2000, 65, 1158-1174]. After cooling to room temperature the reaction mixture was filtered, the filtrate was concentrated and the residue was adsorbed on silica gel and subjected to flash column chromatography (eluents MeOH/CH2Cl2: 2/98 to 10/90). Fractions containing the product were combined, concentrated and treated with AcOEt/hexanes to afford title compound 417 (370 mg, 50% yield) as a yellow-orange solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.57 (bs, 1H), 8.45 (d, J=5.1 Hz, 1H), 8.22 (dd, J=11.3, 2.5 Hz, 1H), 8.06 (dd, J=8.9, 2.3 Hz, 1H), 7.83 (d, J=1.2 Hz, 1H), 7.70 (d, J=1.2 Hz, 1H), 7.63 (s, 1H), 7.24 (t, J=8.7 Hz, 1H), 6.94 (bd, J=4.7 Hz, 1H), 3.71 (s, 3H). LCMS: 370.0 (M+H)+.

1. customwas degassed for 15 min with nitrogen
2. temperatureAfter cooling to room temperature the reaction mixture
3. filtrationwas filtered
4. concentrationthe filtrate was concentrated
5. additionFractions containing the product
6. concentrationconcentrated
7. additiontreated with AcOEt/hexanes