Paper
NJC
7.42 (distorted d, J = 7.6 Hz, 4H), 7.31 (t, J = 8.0, 7.2 Hz, 1H), 3.75 9.46 (bs, 1H), 7.69 (d, J = 7.2 Hz, 2H), 7.45 (d, J = 6.8 Hz, 1H),
(s, 3H); 13C NMR (100 MHz, CDCl3) d 189.12, 160.77, 140.31, 7.37–7.25 (m, 5H), 6.94 (t, J = 8.0 Hz, 2H), 3.74 (s, 3H); 13C NMR
138.41, 134.46, 132.33, 131.21, 130.35, 129.78, 129.41, 128.17, (100 MHz, CD3OD) d 192.40, 162.10 (d, JC–F = 243.7 Hz), 161.06,
127.28, 124.48, 121.21, 119.12, 111.04, 52.06; HRMS (ESI): calc. 139.18, 132.11 (d, JC–F = 8.1 Hz), 131.86, 131.41, 129.92, 128.99,
for [(C20H13ClN2O3)H] [M + H]+ 365.0693, found 365.0665.
128.86, 127.90, 124.13, 120.83, 113.53 (d, JC–F = 21.5 Hz), 50.47;
Methyl 3-(4-fluorophenyl)-4-(4-methylbenzoyl)-1H-pyrrole-2- HRMS (ESI): calc. for [(C19H14FNO3)H] [M + H]+ 324.1036, found
carboxylate 4d. White solid, mp 128–130 1C; IR (ATR) n~ (cmꢀ1): 324.1005.
3316, 1728, 1692, 1634, 1517, 1263 and 841; 1H NMR (400 MHz,
Methyl 4-(3-chlorobenzoyl)-3-(4-fluorophenyl)-1H-pyrrole-2-
CDCl3) d 9.56 (bs, 1H), 7.62 (d, J = 7.2 Hz, 2H), 7.34 (s, 1H), carboxylate 4j. Off white solid mp 104–106 1C; IR (ATR) n~
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7.28 (distorted t, J = 6.4. 6.0 Hz, 2H), 7.15 (d, J = 7.2 Hz, 2H), 6.95 (cmꢀ1): 3296, 1715, 1686, 1637, 1513, 1260 and 739; H NMR
(t, J = 8.4, 8.0 Hz, 2H), 3.74 (s, 3H), 2.37 (s, 3H); 13C NMR (400 MHz, CDCl3) d 9.60 (bs, 1H), 7.61 (s, 1H), 7.55 (d, J = 7.6 Hz,
(100 MHz, CDCl3) d 190.74, 162.26 (d, JC–F = 248.3 Hz), 161.25, 1H), 7.41 (d, J = 3.2 Hz, 2H), 7.28 (s, 3H), 6.95 (t, J = 8.8, 8.4 Hz,
143.01, 136.26, 132.04 (d, JC–F = 8.0 Hz), 131.99, 131.45, 129.65, 2H), 3.74 (s, 3H); 13C NMR (100 MHz, CDCl3) d 189.74, 162.26
129.03, 128.88, 127.36, 125.34, 120.52, 114.40 (d, JC–F = 21.4 Hz), (d, JC–F = 244.8 Hz), 161.18, 140.42, 134.24, 132.08, 132.05
51.78, 21.64; HRMS (ESI): calc. for [(C20H16FNO3)H] [M + H]+ (d, JC–F = 7.9 Hz), 131.31, 129.55, 129.51, 128.79, 127.79, 127.34,
338.1192, found 338.1163.
Methyl 3-(4-bromophenyl)-4-(4-methylbenzoyl)-1H-pyrrole-2- for [(C19H13ClFNO3)H] [M + H]+ 358.0656, found 358.0623.
carboxylate 4e. Pale yellow solid, mp 166–168 1C; IR (ATR) n~ Methyl 3-(4-bromophenyl)-4-(3-chlorobenzoyl)-1H-pyrrole-2-
124.83, 120.79, 114.46 (d, JC–F = 21.3 Hz), 51.88; HRMS (ESI): calc.
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(cmꢀ1): 3262, 1730, 1692, 1636, 1504, 1261 and 754; H NMR carboxylate 4k. White solid, mp 144–146 1C; IR (ATR) n~ (cmꢀ1):
(400 MHz, CDCl3) d 9.57 (bs, 1H), 7.62 (d, J = 8.0 Hz, 2H), 3298, 1730, 1698, 1630, 1505, 1255 and 744; 1H NMR (400 MHz,
7.39 (d, J = 8.0 Hz, 2H), 7.33 (d, J = 2.4 Hz, 1H), 7.20–7.15 (dd, CDCl3) d 9.69 (bs, 1H), 7.62 (s, 1H), 7.56 (d, J = 7.6 Hz, 1H), 7.44–
J = 8.4, 8.0 Hz, 4H), 3.73 (s, 3H), 2.38 (s, 3H); 13C NMR 7.38 (m, 4H), 7.28 (t, J = 7.6 Hz, 1H), 7.16 (d, J = 8.4 Hz, 2H), 3.74
(100 MHz, CDCl3) d 190.57, 161.21, 143.10, 136.23, 132.21, (s, 3H); 13C NMR (100 MHz, CDCl3) d 189.48, 161.11, 140.43,
132.04, 131.21, 130.57, 129.64, 128.94, 127.49, 125.19, 121.59, 134.31, 132.10, 131.98, 131.93, 131.09, 130.63, 129.63, 129.49,
120.54, 51.84, 21.66; HRMS (ESI): calc. for [(C20H16BrNO3)H] 127.89, 127.34, 124.65, 121.76, 120.85, 51.94; HRMS (ESI): calc.
[M + H]+ 398.0392, found 400.0354.
for [(C19H13BrClNO3)H] [M + H]+ 417.9845, found 417.9822.
Methyl 4-benzoyl-3-(4-bromophenyl)-1H-pyrrole-2-carboxylate
Methyl 4-acetyl-3-phenyl-1H-pyrrole-2-carboxylate 4l. White
4f. Off white solid, mp 162–164 1C; IR (ATR) n~ (cmꢀ1): 3275, 1723, solid, mp 170–172 1C; IR (ATR) n~ (cmꢀ1): 3250, 1728, 1697,
1695, 1632, 1505, 1262 and 732; 1H NMR (400 MHz, CDCl3) 1638, 1512, 1270 and 768; 1H NMR (400 MHz, CDCl3) d 9.81
d 9.63 (bs, 1H), 7.71 (d, J = 7.6 Hz, 2H), 7.48 (t, J = 7.2 Hz, 1H), (bs, 1H), 7.54 (d, J = 3.5 Hz, 1H), 7.37–7.34 (m, 3H), 7.30–7.28
7.40–7.34 (m, 5H), 7.19 (d, J = 8.0 Hz, 2H), 3.73 (s, 3H); 13C NMR (m, 2H), 3.63 (s, 3H), 2.02 (s, 3H); 13C NMR (100 MHz, CDCl3) d
(100 MHz, CDCl3) d 190.88, 161.20, 138.92, 132.28, 132.14, 194.43, 161.27, 134.02, 131.33, 129.83, 127.56, 127.47, 126.80,
132.03, 131.25, 130.57, 129.42, 128.25, 127.87, 124.99, 121.63, 126.37, 120.79, 51.49, 29.06; HRMS (ESI): calc. for [(C14H13NO3)]
120.69, 51.87; HRMS (ESI): calc. for [(C19H14BrNO3)H] [M + H]+ [M]ꢀ 243.0895 found 243.0817.
384.0235, found 386.0194.
Methyl 4-acetyl-3-(p-tolyl)-1H-pyrrole-2-carboxylate 4m. White
Methyl 4-benzoyl-3-(4-chlorophenyl)-1H-pyrrole-2-carboxylate solid, mp 184–186 1C; IR (ATR) n~ (cmꢀ1): 3253, 1726, 1694, 1642,
4g. Off white solid, mp 148–150 1C; IR (ATR) n~ (cmꢀ1): 3276, 1516, 1268 and 765; H NMR (400 MHz, CDCl3) d 9.85 (bs, 1H),
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1722, 1689, 1631, 1505, 1263 and 728; 1H NMR (400 MHz, CDCl3) 7.52 (d, J = 3.4 Hz, 1H), 7.24–7.15 (m, 4H), 3.64 (s, 3H), 2.37
d 9.45 (bs, 1H), 7.71 (d, J = 7.2 Hz, 2H), 7.48 (distorted t, J = 7.2, 6.8 (s, 3H), 2.03 (s, 3H); 13C NMR (100 MHz, CDCl3) d 194.61, 161.24,
Hz, 1H), 7.36 (distorted t, J = 7.6, 7.2 Hz, 3H), 7.25 (s, 4H), 3.75 137.11, 131.55, 130.83, 129.70, 128.33, 126.81, 126.41, 120.69,
(s, 3H); 13C NMR (100 MHz, CDCl3) d 190.89, 161.19, 138.91, 133.33, 51.44, 29.10, 21.24; HRMS (ESI): calc. for [(C15H15NO3)–H]
132.27, 131.71, 131.63, 131.24, 129.42, 128.23, 127.78, 127.64, [M ꢀ H]ꢀ 256.0973, found 256.0977.
125.08, 120.72, 51.86; HRMS (ESI): calc. for [(C19H14ClNO3)H]
[M + H]+ 340.0740, found 340.0714.
Methyl 4-acetyl-3-(m-tolyl)-1H-pyrrole-2-carboxylate 4n. White
solid, mp 170–172 1C; IR (ATR) n~ (cmꢀ1): 3259, 1732, 1696, 1635,
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Methyl 4-(3-chlorobenzoyl)-3-(4-chlorophenyl)-1H-pyrrole-2- 1508, 1260 and 772; H NMR (400 MHz, CDCl3) d 9.54 (bs, 1H),
carboxylate 4h. White solid, mp 110–112 1C; IR (ATR) n~ 7.54 (d, J = 3.5 Hz, 1H), 7.27 (d, J = 7.5 Hz, 1H), 7.15 (d, J = 7.6 Hz,
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(cmꢀ1): 3282, 1724, 1691, 1637, 1507, 1258 and 742; H NMR 1H), 7.10–7.08 (m, 2H), 3.65 (s, 3H), 2.36 (s, 3H), 1.99 (s, 3H); 13
C
(400 MHz, CDCl3) d 9.66 (bs, 1H), 7.62 (s, 1H), 7.57 (d, J = 7.6 Hz, NMR (100 MHz, CDCl3) d 194.51, 161.13, 137.05, 133.79, 131.49,
1H), 7.43 (d, J = 8.0 Hz, 2H), 7.30–7.23 (m, 5H), 3.74 (s, 3H); 130.48, 128.28, 127.47, 127.05, 126.90, 126.01, 120.69, 51.46,
13C NMR (100 MHz, CDCl3) d 189.52, 161.11, 140.42, 134.30, 29.10, 21.32; HRMS (ESI): calc. for [(C15H15NO3)–H] [M ꢀ H]ꢀ
133.48, 132.10, 131.68, 131.42, 131.09, 129.61, 129.49, 127.83, 256.0973, found 256.0974.
127.69, 127.34, 124.72, 120.88, 51.92; HRMS (ESI): calc. for
[(C19H13Cl2NO3)H] [M + H]+ 374.0350, found 374.0321.
Methyl 4-acetyl-3-(o-tolyl)-1H-pyrrole-2-carboxylate 4o. White
solid, mp 162–164 1C; IR (ATR) n~ (cmꢀ1): 3248, 1731, 1687,
Methyl 4-benzoyl-3-(4-fluorophenyl)-1H-pyrrole-2-carboxylate 1629, 1502, 1255 and 774; 1H NMR (400 MHz, CDCl3) d 9.77
4i. White solid, mp 128–130 1C; IR (ATR) n~ (cmꢀ1): 3275, 1718, (bs, 1H), 7.61 (d, J = 3.5 Hz, 1H), 7.27–7.16 (m, 3H), 7.11
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1686, 1631, 1510, 1264 and 734; H NMR (400 MHz, CDCl3) d (d, J = 7.9 Hz, 1H), 3.61 (s, 3H), 2.07 (s, 3H), 1.92 (s, 3H); 13C NMR
New J. Chem.
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