3.2.8. Synthesis Method of the Target Compounds **C1–C10**, **D1–D6**

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

#### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)acetamide (**C1**)

Yield, 83%; yellow solid, m.p. 324–325 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 8.25 (d, *J* = 8.3 Hz, 1H), 7.98 (d, *J* = 8.7 Hz, 1H), 7.86 (t, *J* = 7.6 Hz, 1H), 7.75 (d, *J* = 8.2 Hz, 1H), 7.55 (s, 1H), 7.53 (s, 1H), 7.14 (d, *J* = 8.1 Hz, 1H), 4.29 (s, 3H), 2.32 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 169.34, 157.58, 155.96, 137.63, 132.79, 131.55, 126.10, 125.27, 122.69, 122.23, 120.05, 119.93, 119.20, 118.92, 116.85, 115.74, 33.40, 23.88. MS-ESI *m*/*z*: calcd for C18H14ClN3O[M + H]+: 324.0825; found: 324.1824.

#### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)benzamide (**C2**)

Yield, 89%; yellow solid, m.p. 275–277 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 11.96 (s, 1H), 8.57 (d, *J* = 8.5 Hz, 1H), 8.46 (d, *J* = 8.8 Hz, 1H), 8.30 (d, *J* = 7.6 Hz, 2H), 8.20 (t, *J* = 8.0 Hz, 1H), 7.86 (s, 1H), 7.81–7.74 (m, 4H), 7.74–7.64 (m, 2H), 7.51 (d, *J* = 8.5 Hz, 1H), 4.58 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 166.35, 149.50, 143.45, 141.47, 137.27, 134.48, 134.27, 133.44, 133.12, 129.36 (2C), 129.03 (2C), 126.96, 126.22, 126.08, 123.81, 121.10, 118.86, 117.74, 116.96, 113.04, 37.82. MS-ESI *m*/*z*: calcd for C23H16ClN3O[M + H]+: 386.0982; found: 387.2003.

#### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-2-fluorobenzamide (**C3**)

Yield, 64%; brownish red solid, m.p. 361–362 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 11.94 (s, 1H), 8.54 (d, *J* = 8.4 Hz, 1H), 8.40 (d, *J* = 8.8 Hz, 1H), 8.15 (m, 1H), 8.01 (t, *J* = 7.4, 1H), 7.90 (d, *J* = 8.4 Hz, 1H), 7.85 (t, *J* = 7.7 Hz, 1H), 7.81 (s, 1H), 7.79–7.72 (m, 1H), 7.51 (m, 3H), 4.55 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 163.70, 161.20, 158.71, 141.87, 137.34, 134.39, 134.33, 134.25, 133.87, 130.97, 126.41, 126.14, 125.72, 125.46 (d, *J* = 3.3 Hz), 123.07, 121.71, 120.41, 119.44, 117.52, 117.17, 116.95, 113.78, 37.14. MS-ESI *m*/*z*: calcd for C23H15ClFN3O[M + H]+: 404.0888; found: 404.1265.

#### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-3-fluorobenzamide (**C4**)

Yield, 77%; light yellow solid, m.p. > 400 ◦C; 1H NMR (400 MHz, DMSO-*d*6) *δ* 11.98 (s, 1H), 8.66–8.49 (m, 1H), 8.43 (d, *J* = 8.9 Hz, 1H), 8.28–8.00 (m, 3H), 7.92–7.68 (m, 5H), 7.56 (d, *J* = 62.1 Hz, 1H), 4.55 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 165.07, 159.83, 155.64, 143.30, 137.30, 134.49, 134.85, 134.50, 131.56, 129.78, 126.86, 126.07, 125.89, 125.19 (d, *J* = 5.4 Hz), 123.50, 122.07, 120.84, 118.93, 117.57, 115.95, 115.71, 113.50, 37.26. MS-ESI *m*/*z*: calcd for C23H15ClFN3O[M + H]+: 404.0876; found: 404.1280.

### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-4-fluorobenzamide (**C5**)

Yield, 71%; yellow solid, m.p. > 400 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 11.98 (s, 1H), 8.57 (d, *J* = 8.4 Hz, 1H), 8.46 (d, *J* = 8.9 Hz, 1H), 8.39 (d, *J* = 8.6 Hz, 2H), 8.21 (t, *J* = 8.0 Hz, 1H), 7.88 (t, *J* = 7.9 Hz, 1H), 7.84 (s, 1H), 7.73 (d, *J* = 8.5 Hz, 1H), 7.59–7.45 (m, 3H), 4.57 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 165.28, 159.56, 149.61, 143.39, 143.26, 137.27, 134.53, 134.30, 131.97 (2C, d, *J* = 9.7 Hz), 129.63, 126.97, 126.18 (d, *J* = 9.1 Hz), 123.82, 121.05, 118.85, 117.74, 116.98, 116.49 (2C), 116.27, 113.06, 37.73. MS-ESI *m*/*z*: calcd for C23H15ClFN3O[M + H]+: 404.0891; found: 404.1273.

#### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-2-methoxybenzamide (**C6**)

Yield, 65%; orange solid, m.p. 250–252 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 11.51 (s, 1H), 8.52 (d, *J* = 8.3 Hz, 1H), 8.38 (d, *J* = 8.8 Hz, 1H), 8.15 (t, *J* = 7.9 Hz, 1H), 8.00 (d, *J* = 8.4 Hz, 1H), 7.87 (t, *J* = 7.0 Hz, 2H), 7.80 (s, 1H), 7.66 (t, *J* = 7.9 Hz, 1H), 7.53 (d, *J* = 8.4 Hz, 1H), 7.36 (d, *J* = 8.4 Hz, 1H), 7.20 (t, *J* = 7.5 Hz, 1H), 4.54 (s, 3H), 4.08 (s, 3H). 13C NMR (100 MHz, DMSO-*d*6) *δ* 165.38, 157.34, 141.73, 137.27, 134.21, 133.74, 133.53, 130.50, 129.15, 126.55, 126.44, 125.66, 124.01, 123.05, 121.30, 120.61, 119.69, 117.45, 113.64, 112.73, 104.16, 99.82, 56.61, 37.11. MS-ESI *m*/*z*: calcd for C24H18ClN3O2[M + H]+: 416.1088; found: 416.1328.

#### N-(8-chloro-5-methyl-5H-indolo[2,3-b]quinolin-11-yl)-3-methoxybenzamide (**C7**)

Yield, 69%; yellow solid, m.p. 240–241 ◦C (DMSO); 1H NMR (400 MHz, DMSO-*d*6) *δ* 11.95 (s, 1H), 8.59–8.51 (m, 1H), 8.44 (d, *J* = 8.8 Hz, 1H), 8.19 (t, *J* = 8.7, 7.1, 1.5 Hz, 1H), 7.90–7.84 (m, 3H), 7.82 (s, 1H), 7.74 (d, *J* = 8.4 Hz, 1H), 7.61 (t, *J* = 8.0 Hz, 1H), 7.51 (d, *J* = 8.4 Hz, 1H), 7.34 (d, *J* = 8.3 Hz, 1H), 4.57 (s, 3H), 3.92 (s, 4H). 13C NMR (100 MHz, DMSO-*d*6) δ 166.06, 159.98, 140.92, 137.28, 134.45, 134.20, 133.12, 130.56, 128.73, 126.94, 126.07, 125.39, 124.34, 123.70, 121.23, 121.02, 119.37, 117.68, 113.97, 113.20, 105.64, 99.99, 56.04, 37.67. MS-ESI *m*/*z*: calcd for C24H18ClN3O2[M + H]+: 416.1081; found: 416.1336.
