1,3-Dichloro-5-ethynylbenzene → 3-(3,5-Dichlorophenyl)-1-(7-methoxyquinolin-3-yl)prop-2-yn-1-one

To a solution of the 1,3-dichloro-5-ethynylbenzene (185 mg, 1.08 mmol) in anhydrous THF cooled to −78° C. under a N2 atmosphere was added nButLi (750 μL, 1.18 mmol). After 5 minutes, a solution of the intermediate from step E (320 mg, 1.3 mmol) in THF (5 mL) was added. The reaction was gradually warmed to room temperature over 30 minutes and quenched with saturated NH4Cl solution. The resulting bi-phasic mixture was extracted with ethyl acetate, washed with saturated NaCl solution, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 20% ethyl acetate-hexanes to afford the product as a light yellow solid. 1H NMR (500 MHz, CDCl3): 9.54 (d, J=2.3 Hz, 1H), 8.85 (d, J=2.1 Hz, 1H), 7.92 (d, J=9.2 Hz, 1H), 7.62 (d, J=2.0 Hz, 2H), 7.5 (m, 2H), 7.34 (dd, J=2.5, 8.9 Hz, 1H), 4.04 (s, 3H). LC-MS: 3.92 min; (M+H)=356.0.