# The Synthesis and Biological Evaluation of 2-(1H-Indol-3-yl)quinazolin-4(3H)-One Derivatives
## 3 Materials and Methods
#### Synthesis of 2-(1\(H\)-indol-3-yl)quinazolin-4(3\(h\))-one (**3a**) [80]
2-(1-Phenyl-1H-indol-3-yl)quinazolin-4(3H)-one (**3g**). A yield of 0.377 g (86%), 14 h, pale yellow solid. Mp. = 344-345 \({}^{\circ}\)C (EtOH). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.14 (brs., 1H), 8.86 (s, 1H), 8.84-8.82 (m, 1H), 8.14 (br.d, \(J\) = 8.0 Hz, 1H), 7.84-7.78 (m, 2H), 7.71-7.67 (m, 4H), 7.65-7.61 (m, 1H), 7.53-7.50 (m, 1H), 7.48-7.45 (m, 1H), and 7.37-7.35 (m, 2H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.9, 138.9, 138.1, 136.1, 134.3, 131.7, 130.0 (2C), 127.4, 127.1, 126.6, 125.7, 125.5, 124.0 (2C), 123.7, 122.9, 122.0, 120.6, 110.8, 110.6, and 110.1 ppm. HRMS (ESI) Calcd for C\({}_{22}\)H\({}_{16}\)N\({}_{3}\)O [M + H]\({}^{+}\) 338.1288; Found 338.1288. 2-(5-Iodo-1H-indol-3-yl)quinazolin-4(3H)-one (**3k**) [8]. A yield of 0.478 g (95%), 14.5 h, beige solid. Mp. \(\geq\) 308 \({}^{\circ}\)C, decomposition (EtOH, lit. [8] 309-311 \({}^{\circ}\)C). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.13 (brs., 1H), 11.98 (brs., 1H), 9.06 (d, \(J\) = 1.6 Hz, 1H), 8.53 (s, 1H), 8.12 (dd, \(J\) = 8.0, 0.8 Hz, 1H), 7.81-7.78 (m, 1H), 7.73-7.70 (m, 1H), 7.51 (dd, \(J\) = 8.4, 1.6 Hz, 1H), 7.45-7.41 (m, 1H), and 7.36 (d, \(J\) = 8.4 Hz, 1H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.9, 149.8, 149.4, 135.9, 134.3, 130.63, 130.56, 129.8, 127.9, 126.9, 125.7, 125.2, 120.4, 114.4, 107.8, and 85.1 ppm. 2-(5-Bromo-1H-indol-3-yl)quinazolin-4(3H)-one (**3l**). A yield of 0.331 g (75%), 14 h, beige solid. Mp. \(\geq\) 340 \({}^{\circ}\)C, decomposition (EtOH). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.14 (brs., 1H), 12.01 (brs., 1H), 8.85 (d, \(J\) = 1.6 Hz, 1H), 8.58 (s, 1H), 8.12 (dd, \(J\) = 8.0, 0.8 Hz, 1H), 7.81-7.72 (m, 2H), 7.47 (d, \(J\) = 8.4 Hz, 1H), 7.45-7.41 (m, 1H), and 7.37 (dd, \(J\) = 8.8, 2.0 Hz, 1H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.9, 149.8, 149.4, 135.5, 134.3, 130.2, 127.2, 126.9, 125.7, 125.2, 125.1, 124.4, 120.4, 114.0, 113.6, and 108.2 ppm. HRMS (ESI) Calcd for C\({}_{16}\)H\({}_{11}\)BrN\({}_{3}\)O [M + H]\({}^{+}\) 340.0080; Found 340.0080. 2-(2-Phenyl-1H-indol-3-yl)quinazolin-4(3H)-one (**3m**) was determined using GC/MS in trace amounts. Quinazolin-4(3\(H\))-one (**5a**) was isolated as by-product in the synthesis of 2-(2-phenyl-1\(H\)-indol-3-yl)quinazolin-4(3\(H\))-one (**3m**) in a 37% yield. All the spectral data of quinazolin-4(3\(H\))-one (**5a**) were consistent with those described above. 2-[2-(4-Nitrophenyl)-1H-indol-3-yl]quinazolin-4(3H)-one (**3n**) was determined using GC/MS in trace amounts. Quinazolin-4(3\(H\))-one (**5a**) was isolated as by-product in the synthesis of 2-[2-(4-nitrophenyl)-1\(H\)-indol-3-yl]quinazolin-4(3\(H\))-one (**3n**) in a 59% yield. All the spectral data of quinazolin-4(3\(H\))-one (**5a**) were consistent with those described above. 6-Chloro-2-(1H-indol-3-yl)quinazolin-4(3\(H\))-one (**3o**). A yield of 0.350 g (91%), 20 h, pale beige solid. Mp. \(\geq\) 390 \({}^{\circ}\)C, decomposition (EtOH). \({}^{1}\)H NMR (400 MHz, DMSO-\(d_{6}\)) \(\delta\) = 12.24 (brs., 1H), 11.85 (brs., 1H), 8.68 (br.d, \(J\) = 6.8 Hz, 1H), 8.55 (d, \(J\) = 2.0 Hz, 1H), 8.04 (s, 1H), 7.79-7.73 (m, 2H), 7.49 (br.d, \(J\) = 6.8 Hz, 1H), and 7.26-7.20 (m, 2H) ppm; \({}^{13}\)C[\({}^{1}\)H] NMR (100 MHz, DMSO-\(d_{6}\)) \(\delta\) = 161.1, 150.7, 148.4, 136.8, 134.3, 129.4, 129.1, 129.0, 125.4, 124.7, 122.6, 122.3, 121.5, 120.9, 111.9, and 108.3 ppm. HRMS (ESI) Calcd for C\({}_{16}\)H\({}_{11}\)ClN\({}_{3}\)O [M + H]\({}^{+}\) 296.0585; Found 296.0582. 2-(1H-Indol-3-yl)-6-iodoquinazolin-4(3H)-one (**3a**). A yield of 0.226 g (45%), 32 h, pale brown solid. Mp. \(\geq\) 308 \({}^{\circ}\)C, decomposition (1,4-dioxane/EtOH).