8-chloro-11-(4-fluorophenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A4**)

Yield, 76%; yellow solid, m.p. 255–256 ◦C (DMSO); 1H NMR (400 MHz, Chloroform-*d*) *δ* 8.21–8.15 (m, 1H), 7.86–7.77 (m, 2H), 7.66 (s, 1H), 7.44 (d, *J* = 8.1 Hz, 1H), 7.32 (d, *J* = 8.3 Hz, 1H), 7.03–6.92 (m, 5H), 4.38 (s, 3H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 158.63, 157.54, 156.22, 153.76, 152.03, 150.41, 137.15, 133.56, 130.49, 123.44, 123.33, 121.34, 119.38, 116.52, 116.13, 115.80, 115.72, 115.70, 115.62, 115.57, 115.52, 113.52, 32.34. MS-ESI *m*/*z*: calcd for C22H14ClFN2O[M + H]+: 377.0763; found: 377.1875.

#### 8-chloro-11-(2-methoxyphenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A5**)

Yield, 78%; yellow solid, m.p. 244–247 ◦C (DMSO); 1H NMR (400 MHz, Chloroform-*d*) *δ* 8.25 (d, *J* = 8.2 Hz, 1H), 7.79 (d, *J* = 3.5 Hz, 2H), 7.67 (s, 1H), 7.41 (d, *J* = 8.1 Hz, 1H), 7.36 (d, *J* = 8.2 Hz, 1H), 7.13 (d, *J* = 8.2 Hz, 1H), 7.10–7.04 (m, 1H), 6.98 (d, *J* = 8.2 Hz, 1H), 6.69 (t, *J* = 7.8 Hz, 1H), 6.58 (d, *J* = 8.1 Hz, 1H), 4.39 (s, 3H), 4.05 (s, 3H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 157.89, 154.14, 151.28, 148.00, 145.27, 137.12, 133.27, 130.27, 123.68, 123.37, 122.94, 121.14, 120.07, 119.84, 119.19, 116.46, 116.26, 115.49, 114.58, 113.34, 111.91, 55.27, 32.17. MS-ESI *m*/*z*: calcd for C23H17ClN2O2[M + H]+: 389.0979; found: 389.2214.

#### 8-chloro-11-(3-methoxyphenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A6**)

Yield, 83%; orange solid, m.p. 223–224 ◦C (DMSO); 1H NMR (400 MHz, Chloroform-*d*) *δ* 8.21–8.16 (m, 1H), 7.80 (d, *J* = 6.2 Hz, 2H), 7.67 (s, 1H), 7.45–7.36 (m, 2H), 7.17 (t, *J* = 8.3 Hz, 1H), 7.00 (d, *J* = 8.2 Hz, 1H), 6.64 (d, *J* = 8.2 Hz, 1H), 6.60 (t, *J* = 2.4 Hz, 1H), 6.52 (d, *J* = 8.1 Hz, 1H), 4.37 (s, 3H), 3.74 (s, 4H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 161.22, 158.58, 158.11, 154.72, 151.35, 138.14, 134.47, 131.41, 130.59, 124.59, 124.48, 122.32, 120.60, 120.41, 117.42, 117.33, 116.80, 114.47, 108.52, 107.70, 102.27, 55.45, 33.35. MS-ESI *m*/*z*: calcd for C23H17ClN2O2[M+H]+: 389.0961; found: 389.2096.
