Reaction Steps
Intermediate 94 (206 mg, 0.258 mmol) was combined with (R)-8-(benzyloxy)-5-[2-bromo-1-[(tert-butyldimethylsilyl)oxy]ethyl]quinolin-2(1H)-one (115 mg, 0.235 mmol), sodium iodide (20 mg, 0.133 mmol), and K2CO3 (97 mg, 0.705 mmol) in a mixture of anhydrous acetonitrile (1.0 mL) and anhydrous DMF (0.5 mL) and was heated to 100° C. in a microwave for 2 h. The reaction was poured into H2O and extracted repeatedly into EtOAc. Flash chromatography (0-15% MeOH/CH2Cl2) gave the title compound as a yellow solid, 98 mg. 1H NMR (400 MHz, DMSO-d6) δ 10.81 (s, 1H), 10.54 (br s, 1H), 10.45 (s, 1H), 9.09 (s, 1H), 8.36 (d, J=1.7 Hz, 1H), 8.29-8.34 (m, 2H), 8.27 (d, J=10.0 Hz, 1H), 8.21 (dt, J=7.8, 1.3 Hz, 1H), 8.02-8.05 (m, 1H), 7.85-7.89 (m, 1H), 7.78 (br s, 1H), 7.75 (t, J=7.9 Hz, 1H), 7.67 (d, J=8.4 Hz, 2H), 7.54-7.58 (m, 2H), 7.33-7.40 (m, 2H), 7.27-7.33 (m, 1H), 7.14-7.20 (m, 3H), 7.11 (t, J=8.1 Hz, 1H), 7.09 (d, J=8.3 Hz, 1H), 6.62-6.68 (m, 2H), 6.54 (d, J=9.9 Hz, 1H), 6.50-6.54 (m, 1H), 5.26 (s, 2H), 5.09-5.17 (m, 1H), 3.60 (s, 3H), 2.72-2.86 (m, 3H), 2.71 (s, 3H), 2.59-2.68 (m, 3H), 0.78 (s, 9H), 0.00 (s, 3H), −0.21 (s, 3H). ES/MS calcd. for C57H61N6O8Ssi+ 1017.4. Found m/z=1017.5 (M+H+).
