Reaction Steps
A solution of 9-benzenesulfonyl-3-chloro-6-(2-phenylethynyl)-9H-pyrido[2,3-b]indole (200 mg, 0.45 mmol, 1 equiv.) in anhydrous ethanol (25 ml) was treated with 10% palladium on carbon (50 mg, 0.047 mmol, 0.1 equiv.) and then stirred at room temperature under an atmosphere of H2 overnight. The reaction mixture was filtered through celite and then concentrated under reduced pressure. The crude product (pale yellow solid) was purified over silica gel chromatography (eluant CH2Cl2/PE 7:3) to afford the product 61 as a white solid (183 mg, 0.41 mmol) in 91% yield. mp=158-162° C.; IR 3057, 3023, 2926, 1494, 1475, 1432, 1376, 1366, 1255, 1182, 1712, 1090, 977, 908, 713, 683 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.48 (d, 1H, J=2.3 Hz, H2), 8.36 (d, 1H, J==8.7 Hz, H8), 8.12 (m, 3H, H4+H7+CHP), 7.67 (s, 1H, H5), 7.56-7.52 (m, 1H, CHP+CHPh), 7.45-7.38 (m, 3H, 3CHP or CHPh), 7.32-7.18 (m, 5H, CHP+CHPh), 3.12-2.97 (m, 4H, 2CH2); 13C NMR (75 MHz, CDCl3) δ 149.2 (C), 145.4 (CH), 141.4 (C), 138.7 (C), 138.1 (C), 137.0 (C), 134.2 (CH), 130.0 (CH), 129.1 (2×CH), 128.6 (2×CH), 128.6 (2×CH), 128.9 (2×CH), 127.6 (CH), 127.5 (C), 126.3 (CH), 122.0 (C), 120.6 (CH), 120.0 (C), 115.1 (CH), 38.2 (CH2), 38.8 (CH2); MS (+ESI) [M+H+]=447.1
