RSC Advances
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ARTICLE
DOI: 10.1039/C5RA09671E
13C NMR (150 MHz, CDCl3): δ 163.9, 162.3, 144.1, 143.4, HRMS (ESI) Calcd For C28H29FN5 454.2402 (M + H+); Found
137.1, 133.2, 130.5, 130.4, 128.9, 128.6, 128.3, 127.9, 126.8, 454.2402.
125.8, 122.9, 122.2, 121.6, 119.9, 116.3, 116.2, 116.1, 53.7,
2-(1-benzyl-1
benzyl)imidazo[1,2-a]pyridine (8n)
Yield 75%, white solid, mp 199ꢀ200 ˚C, H NMR (600 MHz,
CDCl3): δ 8.03 (s, 1H), 7.83 (s, 1H), 7.48 (d, = 9.6 Hz, 1H),
7.39ꢀ7.35 (m, 5H), 7.15 (t, = 7.2 Hz, 1H), 7.11(d, = 9.6 Hz,
1H), 7.02ꢀ6.99 (m, 3H), 5.59 (s, 2H), 4.86 (s, 2H), 2.26 (s, 3H);
13C NMR (150 MHz, CDCl3): δ 144.6, 143.6, 138.7, 136.7,
135.8, 134.5, 129.4, 129.1, 128.9, 128.7, 127.8, 126.0, 125.4,
122.0, 121.7, 120.8, 120.7, 117.6, 54.6, 29.8, 21.6; IR
(KBr)νmax 3047, 2984, 2882, 2801, 1612, 1538, 1512, 1471,
1430, 1338, 1312, 1247, 1166, 1064 cmꢀ1; HRMS (ESI) Calcd
For C24H21ClN5 414.1480 (M + H+); Found 414.1486.
H-1,2,3-triazol-4-yl)-6-chloro-3-(3-methyl
29.8, 18.5; IR (KBr)νmax 3131, 3062, 3025, 2951, 2919, 2845,
1602, 1537, 1511, 1494, 1453, 1343, 1296, 1227, 1065, 1046
cmꢀ1; HRMS (ESI) Calcd For C24H21FN5 398.1776 (M + H+);
Found 398.1776.
1
J
J
J
3-benzyl-2-(1-benzyl-1
[1,2- ]pyridine (8j)
Yield 85%, white solid, mp 242ꢀ243 ˚C, H NMR (400 MHz,
H
-1,2,3-triazol-4-yl)-6-methylimidazo
a
1
CDCl3): δ 8.05 (s, 1H), 7.57 (s, 1H), 7.44 (d,
7.37ꢀ7.36 (m, 5H), 7.25ꢀ7.23 (m, 4H), 7.19 (d,
J
J
= 8.8 Hz, 1H),
= 7.2 Hz, 1H),
6.99 (s, J = 8.8 Hz, 1H), 5.58 (s, 2H), 4.89 (s, 2H), 2.23 (s, 3H);
13C NMR (150 MHz, CDCl3): δ 145.0, 144.3, 137.6, 134.6,
129.3, 128.9, 128.8, 128.6, 128.4, 127.8, 126.6, 122.1, 121.7,
121.4, 119.7, 116.6, 54.5, 29.8, 18.6; IR (KBr)νmax 3145, 3084, 2-(1-benzyl-1
H-1,2,3-triazol-4-yl)-6-chloro-3-(2-methoxy
3062, 3028, 2984, 2915, 2835, 1604, 1538, 1513, 1493, 1454, benzyl)imidazo[1,2-a]pyridine (8o)
1
1343, 1295, 1209, 1047 cmꢀ1; HRMS (ESI) Calcd For C24H22N5 Yield 78%, white solid, mp 203ꢀ204 ˚C, H NMR (600 MHz,
380.1870 (M + H+); Found 380.1871.
CDCl3): δ 8.17 (s, 1H), 8.01 (s, 1H), 7.44 (d,
7.40ꢀ7.35 (m, 5H), 7.18ꢀ7.16 (m, 2H), 7.09 (d,
J
= 9.0 Hz, 1H),
= 9.6 Hz, 1H),
J
3-(4-(tert-butyl)benzyl)-6-methyl-2-(1-(4-methylbenzyl)-1H-
6.91 (d,
J = 8.4 Hz, 1H), 6.77 (t, J = 7.2 Hz, 1H), 5.58 (s, 2H),
1,2,3-triazol-4-yl)imidazo[1,2-
a] pyridine (8k)
4.84 (s, 2H), 3.95 (s, 3H); 13C NMR (150 MHz, CDCl3): δ
156.9, 144.7, 143.3, 135.5, 134.6, 130.2, 129.4, 129.0, 128.7,
128.1, 125.8, 125.4, 122.6, 121.9, 121.7, 121.2, 120.4, 117.4,
110.6, 55.5, 54.6, 29.9; IR (KBr)νmax 3042, 2978, 2915, 2890,
2812, 1608, 1539, 1515, 1498, 1471, 1335, 1313, 1229, 1078,
1061 cmꢀ1; HRMS (ESI) Calcd For C24H21ClN5O 430.1429 (M
+ H+); Found 430.1437.
1
Yield 84%, white solid, mp 189ꢀ190 ˚C, H NMR (400 MHz,
CDCl3): δ 8.08 (s, 1H), 7.62 (s, 1H), 7.47 (d,
7.27ꢀ7.23 (m, 4H), 7.18ꢀ7.14 (m, 4H), 7.01 (d,
J
J
= 9.2 Hz, 1H),
= 9.2 Hz, 1H),
5.52 (s, 2H), 4.84 (s, 2H), 2.39 (s, 3H), 2.25 (s, 3H), 1.26 (s,
9H); 13C NMR (100 MHz, CDCl3): δ 149.4, 144.7, 143.9,
138.8, 134.4, 131.6, 129.9, 128.7, 127.9, 125.7, 122.1, 121.8,
121.4, 119.9, 116.4, 54.2, 34.5, 31.5, 31.3, 29.1, 21.3, 18.6; IR
(KBr)νmax 3139, 3051, 3026, 2962, 2923, 2866, 1616, 1539, 2-(2-(1-(4-bromobenzyl)-1
H
-1,2,3-triazol-4-yl)imidazo[1,2-
1515, 1454, 1365, 1342, 1301, 1231, 1047 cmꢀ1; HRMS (ESI)
Calcd For C29H32N5 450.2652 (M + H+); Found 450.2652.
a]pyridin-3-yl)ethanol (9a)
Yield 72%, yellow solid, mp 199ꢀ200 ˚C, H NMR (400 MHz,
1
CDCl3): δ 8.08 (d,
8.0 Hz, 3H), 7.22 (d,
J = 6.4 Hz, 1H), 8.01 (s, 1H), 7.52 (d, J =
3-benzyl-2-(1-(4-bromobenzyl)-1
H
-1,2,3-triazol-4-yl)-6-
J
= 8.0 Hz, 2H), 7.17 (t,
J
J
= 8.8 Hz, 1H),
= 5.6 Hz, 2H),
methylimidazo[1,2- ]pyridine (8l)
a
6.83 (t,
3.60 (d,
J = 6.4 Hz, 1H), 5.53 (s, 2H), 4.09 (d,
J
1
Yield 82%, white solid, mp 179ꢀ180 ˚C, H NMR (400 MHz,
CDCl3): δ 8.19 (s, 1H), 7.54 (s, 1H), 7.48 (d,
= 5.6 Hz, 2H); 13C NMR (100 MHz, CDCl3): δ 145.1,
J
= 9.6 Hz, 1H),
= 8.8 Hz,
144.8, 134.4, 133.5, 132.5, 130.2, 124.6, 123.6, 123.3, 121.8,
119.7, 117.4, 112.5, 61.5, 53.9, 27.1; IR (KBr)νmax3126, 3051,
2923, 2850, 1591, 1503, 1489, 1432, 1407, 1359, 1298, 1226,
1070, 1045 cmꢀ1; HRMS (ESI) Calcd For C18H17BrN5O
398.0611 (M + H+); Found 398.0611.
7.44 (d, = 8.8 Hz, 2H), 7.21ꢀ7.13 (m, 7H), 7.03 (d,
J
J
1H), 5.48 (s, 2H), 4.83 (s, 2H), 2.19 (s, 3H); 13C NMR (150
MHz, CDCl3): δ 144.6, 143.9, 137.4, 133.7, 132.5, 130.2,
128.9, 128.4, 128.3, 126.7, 123.1, 122.5, 122.1, 121.4, 119.9,
116.4, 53.7, 29.9, 18.6; IR (KBr)νmax 3142, 3059, 3025, 2951,
2924, 2853, 1602, 1540, 1512, 1489, 1453, 1342, 1298, 1230, 2-(2-(1-benzyl-1
H
-1,2,3-triazol-4-yl)-6-methylimidazo[1,2-
1046 cmꢀ1; HRMS (ESI) Calcd For C24H21BrN5 458.0975 (M +
H+); Found 458.0979.
a]pyridin-3-yl)ethanol (9b)
1
Yield 74%, yellow solid, mp 119ꢀ120 ˚C, H NMR (400 MHz,
CDCl3): δ 7.99 (s, 1H), 7.82 (s, 1H), 7.41ꢀ7.35 (m, 6H), 7.01 (d,
3-(4-(tert-butyl)benzyl)-2-(1-(4-fluorobenzyl)-1
triazol-4-yl)-6-methylimidazo[1,2- ] pyridine (8m)
Yield 80%, white solid, mp 201ꢀ202 ˚C, H NMR (600 MHz,
H-1,2,3-
J
= 8.4 Hz, 1H), 5.56 (s, 2H), 4.06 (br s, 2H), 3.57 (br s, 2H),
a
2.34 (s, 3H); 13C NMR (100 MHz, CDCl3): δ 144.6, 134.4,
129.4, 129.1, 128.6, 127.7, 122.2, 121.7, 121.1, 116.7, 61.4,
54.6, 27.1, 18.6; IR (KBr)νmax 3145, 3062, 3028, 2923, 2855,
1587, 1540, 1512, 1497, 1455, 1366, 1345, 1303, 1230, 1124,
1046 cmꢀ1; HRMS (ESI) Calcd For C19H20N5O 334.1663 (M +
H+); Found 334.1664.
1
CDCl3): δ 8.15 (s, 1H), 7.64 (s, 1H), 7.50 (d,
7.35ꢀ7.33 (m, 2H), 7.27ꢀ7.25 (m, 2H), 7.14 (d,
J
J
= 9.0 Hz, 1H),
= 7.8 Hz, 2H),
7.06 (t,
J = 8.4 Hz, 3H), 5.55 (s, 2H), 4.85 (s, 2H), 2.26 (s, 3H),
1.26 (s, 9H); 13C NMR (100 MHz, CDCl3): δ 164.3, 161.9,
149.6, 144.3, 143.6, 134.1, 133.3, 130.5, 130.4, 128.7, 127.9,
125.8, 122.7, 122.1, 121.6, 120.1, 116.4, 116.2, 53.7, 34.6,
31.5, 29.9, 18.6; IR (KBr)νmax 3053, 2962, 2920, 2867, 1606,
1545, 1516, 1454, 1420, 1364, 1298, 1225, 1159, 1048 cmꢀ1;
6 | J. Name., 2012, 00, 1-3
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