8-chloro-11-(4-methoxyphenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A7**)

Yield, 76%; yellow solid, m.p. 197–200 ◦C (DMSO); 1H NMR (400 MHz, Chloroform-*d*) *δ* 8.22 (d, *J* = 8.1 Hz, 1H), 7.80 (d, *J* = 7.5 Hz, 2H), 7.65 (s, 1H), 7.42 (d, *J* = 8.2 Hz, 1H), 7.30 (d, *J* = 8.2 Hz, 1H), 6.94 (d, *J* = 9.1 Hz, 2H), 6.86–6.79 (m, 3H), 6.75 (d, *J* = 8.8 Hz, 1H), 4.35 (s, 3H), 3.75 (s, 3H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 158.64, 155.43, 154.49, 152.22, 151.18, 138.15, 134.31, 131.43, 124.71, 124.60, 122.31, 120.59, 120.36, 117.49, 117.30, 116.52 (2C), 116.16, 115.12 (2C), 114.78, 114.49, 58.36, 33.38. MS-ESI *m*/*z*: calcd for C23H17ClN2O2[M+H]+: 389.0975; found: 389.2216.

#### 8-chloro-11-(3,4-dimethoxyphenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A8**)

Yield, 63%; dark brown solid, m.p. 245–249 ◦C (DMSO); 1H NMR (400MHz, Chloroform-*d*) *δ* 8.23 (d, *J* = 8.3 Hz, 1H), 7.86–7.75 (m, 2H), 7.68 (s, 1H), 7.44 (d, *J* = 8.1 Hz, 1H), 7.32 (d, *J* = 8.2 Hz, 1H), 7.00 (d, *J* = 8.2 Hz, 1H), 6.80 (d, *J* = 2.9 Hz, 1H), 6.67 (d, *J* = 9.1 Hz, 1H), 6.31 (d, *J* = 8.8 Hz, 1H), 4.37 (s, 3H), 3.83–3.76 (m, 6H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 158.51, 154.32, 151.96, 151.31, 150.30, 145.13, 138.15, 134.42, 131.49, 124.70, 124.64, 122.37, 120.57, 120.49, 117.45, 117.32, 114.52, 112.45, 111.72, 105.91, 105.89, 101.05, 56.30, 56.16, 33.47. MS-ESI *m*/*z*: calcd for C24H19ClN2O3[M + H]+: 419.1084; found: 419.2344.

#### 8-chloro-5-methyl-11-(p-tolyloxy)-5H-indolo[2,3-b]quinoline (**A9**)

Yield, 74%; brown solid, m.p. 219–220 ◦C (DMSO); 1H NMR (400 MHz, Chloroform-*d*) *δ* 8.23–8.18 (m, 1H), 7.82–7.78 (m, 2H), 7.66 (s, 1H), 7.41 (d, *J* = 8.1 Hz, 1H), 7.33 (d, *J* = 8.3 Hz, 1H), 7.09 (d, *J* = 8.5 Hz, 2H), 6.97 (d, *J* = 8.2 Hz, 1H), 6.92–6.85 (m, 2H), 4.36 (s, 3H), 2.30 (s, 3H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 158.56, 155.07, 154.44, 151.97, 138.14, 134.33, 132.76, 131.44, 130.56 (2C), 129.91, 124.69, 124.54, 122.34, 120.56, 120.37, 117.49, 117.26, 116.44, 115.36 (2C), 114.51, 58.27, 18.36. MS-ESI *m*/*z*: calcd for C23H17ClN2O[M+H]+: 373.1029; found: 373.2255.

#### 8-chloro-11-(4-chlorophenoxy)-5-methyl-5H-indolo[2,3-b]quinoline (**A10**)

Yield, 85%; yellow solid, m.p. 258–262 ◦C (DMSO); 1H NMR (400 MHz, Chloroform*d*) *δ* 8.19–8.12 (m, 1H), 7.83 (d, *J* = 6.2 Hz, 2H), 7.67 (s, 1H), 7.45 (d, *J* = 8.1 Hz, 1H), 7.37 (d, *J* = 8.1 Hz, 1H), 7.28 (s, 1H), 7.02 (d, *J* = 8.2 Hz, 1H), 6.97–6.92 (m, 2H), 6.89–6.81 (m, 1H), 4.38 (s, 3H). 13C NMR (100 MHz, Chloroform-*d*) *δ* 158.40, 155.54, 154.57, 151.09, 134.79, 131.63, 130.16, 129.40, 128.38, 124.39, 124.33, 122.54, 120.63, 120.26, 117.52, 117.07, 116.91, 116.78, 114.64, 33.48. MS-ESI *m*/*z*: calcd for C22H14Cl2N2O[M + H]+: 393.0483; found: 393.1729.

#### 3.2.7. Synthesis Method of Target Compounds **B1–B9**

The Intermediate IV was dissolved in N, N-dimethylformamide (DMF). Then, the corresponding phenylhydrazine compounds were added and reflux at 110 ◦C for 3–6 h. After the reaction, dichloromethane, ethyl acetate and salt water were added to the reaction system for washing, and solids were collected to obtain the target compounds **B1–B9**.

8-chloro-5-methyl-11-(2-phenylhydrazineyl)-5H-indolo[2,3-b]quinoline (**B1**)

Yield, 70%; gray solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 13.86 (s, 1H), 10.96 (s, 1H), 9.16 (s, 1H), 8.82 (d, *J* = 8.6 Hz, 1H), 8.50 (d, *J* = 8.9 Hz, 1H), 8.16 (d, *J* = 8.7 Hz, 1H), 8.04 (t, *J* = 7.9 Hz, 1H), 7.91–7.74 (m, 1H), 7.69 (t, *J* = 7.8 Hz, 1H), 7.62 (s, 1H), 7.21 (m, 2H), 6.86 (m, 2H), 4.57 (s, 1H), 4.26 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 152.82, 149.05, 148.47, 138.82, 137.00, 133.67, 130.70, 130.58, 129.77(2C), 124.76, 124.34, 122.34, 120.90, 120.28, 117.30, 113.87, 113.60(2C), 111.69, 97.44, 36.14. MS-ESI *m*/*z*: calcd for C22H17ClN4[M + H]+: 373.1142; found: 373.2594.
