8-chloro-11-(3-fluorophenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A3**)

Yield, 82%; orange solid, m.p. 250–252 ◦C (DMSO); 1H NMR (400 MHz, Chloroform-*d*) δ 8.18–8.10 (m, 1H), 8.01 (s, 1H), 7.88–7.77 (m, 2H), 7.66 (d, *J* = 1.8 Hz, 1H), 7.44 (d, *J* = 8.1 Hz, 1H), 7.39 (d, *J* = 8.2 Hz, 1H), 7.01 (d, *J* = 8.2 Hz, 1H), 6.85–6.80 (m, 1H), 6.80–6.68 (m, 2H), 4.37 (s, 3H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 164.92, 162.59, 158.43, 154.66, 150.84, 138.14, 134.78, 131.62, 131.09 (d, *J* = 9.7 Hz), 130.21 (d, *J* = 10.2 Hz), 124.31 (d, *J* = 4.4 Hz), 122.55, 120.60, 120.27, 117.51, 117.00, 114.64, 111.15, 111.12, 110.33 (d, *J* = 21.2 Hz), 103.70 (d, *J* = 25.7 Hz), 33.45. MS-ESI *m*/*z*: calcd for C22H14ClFN2O[M + H]+: 377.0781; found:377.1899.
