8-chloro-11-(2-fluorophenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A2**)

Yield, 73%; orange solid, m.p. 325–328 ◦C (DMSO); 1H NMR (400 MHz, Chloroform-*d*) *δ* 8.23 (d, *J* = 8.2, 1.4 Hz, 1H), 7.95 (d, *J* = 8.7 Hz, 1H), 7.89 (d, *J* = 8.7 Hz, 1H), 7.60 (s, 1H), 7.51 (d, *J* = 8.1 Hz, 1H), 7.34 (d, *J* = 8.4 Hz, 1H), 7.31–7.25 (m, 1H), 7.11–7.04 (m, 1H), 7.00 (d, *J* = 8.3 Hz, 1H), 6.92–6.86 (m, 1H), 6.65 (t, *J* = 8.3 Hz, 1H), 4.37 (s, 3H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 158.24, 156.33, 154.27, 152.54, 151.37, 148.13, 140.16, 133.84, 132.32, 131.82, 124.99, 124.30, 121.73, 119.94, 117.85, 117.11, 116.63, 116.14, 115.10, 114.68, 113.32, 34.09. MS-ESI *m*/*z*: calcd for C22H14ClFN2O[M + H]+: 377.0779; found: 377.1835.
