반응 단계
A mixture of 3-diethylamino-7-iodopyrazolo[1,5-a]pyridine (0.074 g, 0.217 mmol), 2,4,6-trimethylphenylboronic acid (0.053 g, 0.325 mmol), potassium phosphate (0.138 g, 0.650 mmol), dicyclohexyl[2-(9-phenanthryl)phenyl]phosphine (0.012 g, 0.026 mmol) and Pd2(dba)3 (0.004 g, 0.004 mmol) in toluene (2.2 mL) was refluxed for 72 h. Additional Pd2(dba)3 (0.004 g, 0.004 mmol) and 2,4,6-trimethylphenylboronic acid (0.053 g, 0.325 mmol) were added and reflux was continued for 42 h. The reaction mixture was diluted with CH2Cl2 and filtered through a bed of celite. The filtrate was concentrated in vacuo to dryness. The residue was subjected to preparative thin layer chromatography (5% ethyl acetate/hexane) to give 0.048 g (66%) of a light yellow oil as the title compound: 1H NMR (400 MHz, CDCl3) δ 7.37 (d, J=8.9 Hz, 1H), 6.95–6.90 (m, 3H), 6.35 (d, J=6.7 Hz, 1H), 3.07 (q, J=7.1 Hz, 4H), 2.66 (q, J=7.6 Hz, 2H), 2.28 (s, 3H), 1.92 (s, 6H), 1.10 (t, J=7.6 Hz, 3H), 0.90 (t, J=7.1 Hz, 6H); 13C NMR (100 MHz, CDCl3) δ 155.6, 137.9, 137.2, 136.6, 135.5, 132.9, 130.0, 127.5, 127.4, 125.0, 124.1, 121.4, 119.7, 117.6, 112.8, 50.3, 20.2, 14.7, 14.5; IR (diffuse reflectance) 2969, 2931, 2898, 2869, 2815, 1627, 1613, 1552, 1524, 1498, 1475, 1456, 1445, 1339, 1306, 1228, 1217, 848, 782 cm−1; MS (EI) m/z 336 (M++H); HRMS (FAB) calcd for C22H29N3+H 336.2440. found 336.2421.
