A mixture of intermediate 15 (150 mg, 0.51 mmol) and NaI (150 mg, 1.0 mmol) in CH3CN was heated to reflux for 30 min and then cooled to rt. Intermediate 31 (130 mg, 0.51 mmol) and anhydrous K2CO3 (282 mg, 2.04 mmol) were added to the mixture. The resulting mixture was heated to reflux and stirred overnight. The reaction solution was diluted with water and extracted with EtOAc. The combined EtOAc layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash chromatography on silica gel column (elution with DCM/MeOH=50:1) to give 7-(4-(4-(2-ethoxyphenyl)-1,4-diazepan-1-yl)butoxy)quinolin-2(1H)-one (compound 14) (50 mg, 24%). 1H NMR (300 MHz, CDCl3) δ 10.89 (bs, 1H), 7.69 (d, J=9.6 Hz, 1H), 7.44 (d, J=9.0 Hz, 1H), 6.92-6.78 (m, 5H), 6.71 (d, J=2.7 Hz, 1H), 6.51 (d, J=9.6 Hz, 1H), 4.10-4.01 (m, 4H), 3.36-3.30 (m, 4H), 2.89-2.79 (m, 4H), 2.62-2.59 (m, 4H), 2.02-2.01 (m, 2H), 1.89-1.82 (m, 2H), 1.45 (t, J=6.9 Hz, 3H). HPLC: 99%, RT 2.375 min. MS (ESI) m/z 436.2 [M+H]+.
