(ppm): 189.44, 152.17 (2C), 139.10, 135.94, 130.98 (2C), 130.89 (2C), 130.62, 125.45, 125.06, 120.43, 119.55, 106.21
(2C), 60.00, 55.71 (2C); ESI-HRMS m/z: calcd for C20H18BrNO4 ([M+H]): 416.0498, 418.0478; found: 416.0518,
418.0500.
3-(4-methylbezoyl)-4-(3,4,5-trimethoxy phenyl)-1H-pyrrole (3g). White solid, yield 76.0 %, mp 214-216 ºC; 1H NMR
(400 MHz, DMSO-d6) (ppm): 11.59 (s, 1H, pyrrole-NH), 7.61 (d, J=8.0 Hz, 2H, -CO-Ar-H), 7.23 (s, 1H, pyrrole H), 7.20
(s, 2H, -CO-Ar-H), 7.11 (s, 1H, pyrrole H), 6.65 (s, 2H, Ar-H), 3.68 (s, 6H, 3’, 5’-OCH3), 3.62 (s, 3H, 4’-OCH3), 2.33 (s,
3H, PhCH3); 13C NMR (100 MHz, DMSO-d6) (ppm): 190.31, 152.17 (2C), 141.46, 137.38, 135.85, 130.85, 129.12 (2C),
128.54 (2C), 127.38, 125.31, 120.83, 119.27, 106.06 (2C), 59.96, 55.69 (2C), 20.97; ESI-HRMS m/z: calcd for
C21H21NO4 ([M+H]): 352.1550; found: 352.1576.
1
3-(2,4-dimethylbezoyl)-4-(3,4,5-trimethoxy phenyl)-1H-pyrrole (3h). White solid, yield 69.1 %, mp 164-166 ºC; H
NMR (400 MHz, DMSO-d6) (ppm): 11.57 (s, 1H, pyrrole-NH), 7.22 (d, J=8.0 Hz, 1H, -CO-Ar-H), 7.06 (s, 1H, pyrrole H),
7.04 (s, 1H, pyrrole-H), 6.97 (s, 2H, -CO-Ar-H), 6.75 (s, 2H, Ar-H), 3.73 (s, 6H, 3’, 5’-OCH3), 3.64 (s, 3H, 4’-OCH3), 2.27
(s, 3H, PhCH3), 2.22 (s, 3H, PhCH3); 13C NMR (100 MHz, DMSO-d6) (ppm): 192.25, 152.06 (2C), 138.62, 138.49,
135.97, 135.17, 131.03, 130.66, 129.09, 128.02, 125.39, 125.22, 122.15, 119.93, 106.27 (2C), 59.96, 55.69 (2C), 20.77,
19.36; ESI-HRMS m/z: calcd for C22H23NO4 ([M+H]): 366.1701; found: 366.1736.
3-(3-methoxybezoyl)-4-(3,4,5-trimethoxy phenyl)-1H-pyrrole (3i). White solid, yield 79.1 %, mp 166-168 ºC; 1H NMR
(400 MHz, DMSO-d6) (ppm): 11.64 (s, 1H, pyrrole-NH), 7.32 (t, J=8.0 Hz, 1H, pyrrole H), 7.28-7.22 ( m, 2H, -CO-Ar-H),
7.15 (s, 1H, pyrrole H), 7.11-7.05 (m, 2H, -CO-Ar-H), 6.63 (s, 2H, Ar-H), 3.72 (s, 3H, -CO-Ar-OCH3), 3.68 (s, 6H, 3’, 5’-
OCH3), 3.61 (s, 3H, 4’-OCH3); 13C NMR (100 MHz, DMSO-d6) (ppm): 190.22, 158.79, 152.15 (2C), 141.47, 135.86,
130.80, 129.09, 127.85, 125.41, 121.33, 120.73, 119.42, 117.45, 113.63, 106.15 (2C), 59.93, 55.68 (2C), 55.09; ESI-
HRMS m/z: calcd for C21H21NO5 ([M+H]): 368.1499; found: 368.1533.
3-(4-methoxybezoyl)-4-(3,4,5-trimethoxy phenyl)-1H-pyrrole (3j). White solid, yield 82.8 %, mp 210-212 ºC; 1H NMR
(400 MHz, DMSO-d6) (ppm): 11.57 (s, 1H, pyrrole-NH), 7.72 (d, J=8.0 Hz, 2H, -CO-Ar-H), 7.21 (s, 1H, pyrrole H), 7.12
(s, 1H, pyrrole H), 6.96 (d, J=8.0 Hz, 2H, -CO-Ar-H), 6.64 (s, 2H, Ar-H), 3.80 (s, 3H, -CO-Ar-OCH3), 3.68 (s, 6H, 3’, 5’-
OCH3), 3.62 (s, 3H, 4’-OCH3); 13C NMR (100 MHz, DMSO-d6) (ppm): 189.54, 162.00, 152.20 (2C), 135.79, 132.46,
131.24 (2C), 130.90, 126.64, 125.18, 120.93, 119.03, 113.27 (2C), 105.96 (2C), 59.95, 55.68 (2C), 55.34; ESI-HRMS
m/z: calcd for C21H21NO5 ([M+H]): 368.1499; found: 368.1538.
1
3-(2-pyridylformyl)-4-(3,4,5-trimethoxy phenyl)-1H-pyrrole (3k). Pale yellow solid, yield 68.3 %, mp 155-157 ºC; H
NMR (400 MHz, DMSO-d6) (ppm): 11.65 (s, 1H, pyrrole-NH), 8.62 (d, J=8.0 Hz, 1H, pyridine H), 7.95 (td, J1=8.0 Hz,
J2=2.0 Hz, 1H, pyridine H), 7.80 (td, J=8.0 Hz, J2=0.8 Hz, 1H, pyridine H), 7.70 (dd, J1=4.0 Hz, J2=2.0 Hz, 1H, pyrrole H),
7.54 (m, 1H, pyridine H), 7.06 (t, J=4.0 Hz, 1H, pyrrole H), 6.72 (s, 2H, Ar-H), 3.75 (s, 6H, 3’, 5’-OCH3), 3.67 (s, 3H, 4’-
OCH3); 13C NMR (100 MHz, DMSO-d6) (ppm): 187.75, 156.93, 152.04 (2C), 148.21, 137.00, 135.92, 131.08, 130.38,
126.07, 125.60, 123.04, 119.38, 119.25, 106.36 (2C), 59.95, 55.73 (2C); ESI-HRMS m/z: calcd for C19H18N2O4 ([M+H]):
339.1346; found: 339.1387.
1
3-(3-pyridylformyl)-4-(3,4,5-trimethoxy phenyl)-1H-pyrrole (3l). Pale yellow solid, yield 50.0 %, mp 163-165 ºC; H
NMR (400 MHz, DMSO-d6) (ppm): 11.77 (s, 1H, pyrrole-NH), 8.80 (s, 1H, pyridine H), 8.68 (dd, J1=4.0 Hz, J2=2.0 Hz,
1H, pyridine H), 8.01 (dt, J1=8.0 Hz, J2=2.0 Hz, 1H, pyridine H), 7.48-7.41 (m, 1H, pyridine H), 7.36 (t, J=4.0 Hz, 1H,
pyrrole H), 7.15 (t, J=4.0 Hz, 1H, pyrrole H), 6.68 (s, 2H, Ar-H), 3.71 (s, 6H, 3’, 5’-OCH3), 3.64 (s, 3H, 4’-OCH3); 13C
NMR (100 MHz, DMSO-d6) (ppm): 188.78, 152.18 (2C), 151.65, 149.36, 136.16, 135.96, 135.58, 130.46, 128.61,
125.46, 123.21, 120.59, 119.84, 106.30 (2C), 59.94, 55.73 (2C); ESI-HRMS m/z: calcd for C19H18N2O4 ([M+H]):
339.1346; found: 339.1390.
3-(2-thienylformyl)-4-(3,4,5-trimethoxy phenyl)-1H-pyrrole (3m). White solid, yield 79.0 %, mp 161-163 ºC; 1H NMR
(400 MHz, DMSO-d6) (ppm): 11.66 (s, 1H, pyrrole-NH), 7.92 (dd, J1=4.0 Hz, J2=1.2 Hz, 1H, thiophene H), 7.65 (dd,
J1=4.0 Hz, J2=1.2 Hz, 1H, thiophene H), 7.50 (t, J=4.0 Hz, 1H, pyrrole H), 7.18 (dd, J1=4.0 Hz, J2=1.2 Hz, 1H, thiophene
H), 7.14 (t, J=4.0 Hz, 1H, pyrrole H), 6.70 (s, 2H, Ar-H), 3.73 (s, 6H, 3’, 5’-OCH3), 3.65 (s, 3H, 4’-OCH3); 13C NMR (100
MHz, DMSO-d6) (ppm): 182.09, 152.25 (2C), 145.65, 135.92, 133.12, 132.98, 130.70, 128.11, 126.50, 125.03, 120.42,
119.47, 105.98 (2C), 59.97, 55.73 (2C); ESI-HRMS m/z: calcd for C18H17NO4S ([M+H]): 344.0957; found: 344.1008.
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