1030, 833, 741 cm-1; HRMS (ESI-TOF) m/z calculated for
cm-1; HRMS (ESI-TOF) m/z calculated for C20H16BrN2Se+ 442.9657
(M+H)+, found 442.9655.
ACCEPTED MANUSCRIPT
C21H19N2OSe+ 395.0657 (M+H)+, found 395.0655.
6-Methyl-2-phenyl-3-(p-tolylselanyl)imidazo[1,2-a]pyridine (2e)
3-((4-Bromophenyl)selanyl)-2-phenylimidazo[1,2-a]pyridine (2k)
Following the general procedure, isolated yield (98.7 mg, 87%) as a
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.18-8.03 (m,
Following the general procedure, isolated yield (100.1 mg, 78%) as a
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.31 (dt, J=6.9,
1
1
3H), 7.61 (dd, J=9.1, 0.9 Hz, 1H), 7.55-7.38 (m, 3H), 7.38-7.32 (m,
1H), 7.15 (dd, J=9.1, 1.8 Hz, 1H), 7.04-6.97 (m, 3H), 2.31 (d, J=1.1
Hz, 3H), 2.25 (s, 3H). 13C-NMR (CDCl3, 100 MHz): 151.4, 146.7,
136.5, 133.9, 130.5, 129.5, 128.7, 128.5, 128.3, 128.2, 127.3, 123.4,
122.7, 116.8, 102.7, 21.0, 18.4. FTIR: 3043, 2919, 1488, 1338, 1242,
1062, 982, 795, 693 cm-1; HRMS (ESI-TOF) m/z calculated for
C21H19N2Se+ 379.0708 (M+H)+, found 379.0709.
1.2 Hz, 1H), 8.17-8.05 (m, 2H), 7.72 (dt, J=9.0, 1.1 Hz, 1H), 7.47-
7.41 (m, 2H), 7.41-7.35 (m, 1H), 7.35-7.26 (m, 3H), 7.01-6.92 (m,
2H), 6.87 (td, J=6.8, 1.2 Hz, 1H). 13C-NMR (CDCl3, 100 MHz):
152.1, 147.9, 133.6, 132.7, 129.9, 129.8, 128.7, 128.6, 128.4, 126.6,
125.4, 120.7, 117.7, 113.2, 102.2. FTIR: 3064, 2923, 2359, 1462,
1339, 1262, 1004, 755, 661 cm-1; HRMS (ESI-TOF) m/z calculated
for C19H14BrN2Se+ 428.9500 (M+H)+, found 428.9503.
3-((4-Methoxyphenyl)selanyl)-2-phenylimidazo[1,2-a]pyridine (2f)
Following the general procedure, isolated yield (102.6 mg, 90%) as a
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.31 (dt, J=6.9,
6-Methyl-2-phenyl-3-(pyridin-4-ylselanyl)imidazo[1,2-a]pyridine (2l)
Following the general procedure, isolated yield (67.9 mg, 62%) as a
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.33 (d, J=5.4
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1
1.2 Hz, 1H), 8.13-8.03 (m, 2H), 7.61 (dd, J=9.0, 1.2 Hz, 1H), 7.43-
7.33 (m, 2H), 7.33-7.25 (m, 1H), 7.26-7.14 (m, 1H), 7.02 (d, J=8.9
Hz, 2H), 6.78 (td, J=6.8, 1.2 Hz, 1H), 6.70-6.59 (m, 2H), 3.62 (s,
3H). 13C-NMR (CDCl3,100Hz): 158.0, 149.7, 146.2, 132.5, 129.8,
127.8, 127.4, 127.3, 125.6, 124.6, 119.3, 116.2, 114.4, 112.1, 103.3,
54.2. FTIR: 2960, 2360, 2341, 1463, 1341, 1246, 1028, 773, 697
cm-1; HRMS (ESI-TOF) m/z calculated for C20H17N2OSe+ 381.0501
(M+H)+, found 381.0503.
Hz, 2H), 8.16-7.97 (m, 3H), 7.67 (d, J=9.1 Hz, 1H), 7.50-7.34 (m,
3H), 7.22 (dd, J=9.2, 1.8 Hz, 1H), 7.06-6.91 (m, 2H), 2.34 (s, 3H).
13C-NMR (CDCl3, 100 MHz): 152.6, 150.0, 147.2, 143.8, 133.5,
130.0, 128.6, 128.5, 128.4, 123.4, 123.0, 122.5, 117.2, 99.7, 18.4.
FTIR: 3039, 2923, 1541, 1477, 1402, 1338, 1249, 798, 690 cm-1;
HRMS (ESI-TOF) m/z calculated for C19H16N3Se+ 366.0504
(M+H)+, found 366.0514.
3-((4-Bromophenyl)selanyl)-2-methylimidazo[1,2-a]pyridine (2m)
6-Bromo-3-((4-(tert-butyl)phenyl)selanyl)-2-phenylimidazo[1,2-
a]pyridine (2g)
Following the general procedure, isolated yield (82.3 mg, 75%) as a
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.18 (dt, J=6.9,
1
Following the general procedure, isolated yield (75.5 mg, 52%) as a
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.46 (dd, J=1.9,
1.2 Hz, 1H), 7.63-7.55 (m, 1H), 7.32-7.21 (m, 3H), 6.97-6.87 (m,
2H), 6.83 (td, J=6.8, 1.2 Hz, 1H), 2.61 (s, 3H). 13C-NMR (CDCl3,
100 MHz): 151.9, 147.7, 132.5, 130.1, 130.0, 126.1, 125.2, 120.7,
116.9, 112.7, 103.9, 14.6. FTIR: 3047, 2922, 1493, 1334, 1266,
1239, 1065, 754, 686 cm-1; HRMS (ESI-TOF) m/z calculated for
C14H12BrN2Se+ 366.9344 (M+H)+, found 366.9348.
1
0.9 Hz, 1H), 8.10 (dd, J=8.4, 1.4 Hz, 2H), 7.58-7.46 (m, 1H), 7.41-
7.33 (m, 2H), 7.33-7.25 (m, 2H), 7.17-7.10 (m, 2H), 6.98 (d, J=8.5
Hz, 2H), 1.17 (s, 9H). 13C-NMR (CDCl3, 100 MHz): 152.2, 150.3,
146.1, 133.4, 129.8, 128.7, 128.7, 128.4, 128.3, 126.9, 126.8, 125.9,
118.1, 107.8, 103.9, 34.5, 31.2. FTIR: 3040, 2960, 1492, 1358, 1215,
1061, 1010, 817, 685 cm-1; HRMS (ESI-TOF) m/z calculated for
C23H22BrN2Se+ 485.0126 (M+H)+, found 485.0131.
6-Methyl-2-phenyl-3-(o-tolylselanyl)imidazo[1,2-a]pyridine (2n)
Following the general procedure, isolated yield (51.0 mg, 45%) as a
1
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.21-8.04 (m,
6-Methyl-3-(naphthalen-1-ylselanyl)-2-phenylimidazo[1,2-a]pyridine
(2h)
3H), 7.66 (d, J=9.1 Hz, 1H), 7.49-7.32 (m, 3H), 7.25-7.15 (m, 2H),
7.11 (td, J=7.4, 1.3 Hz, 1H), 6.91 (td, J=7.6, 1.5 Hz, 1H), 6.57 (dd,
J=7.9, 1.3 Hz, 1H), 2.50 (s, 3H), 2.39-2.27 (m, 3H). 13C-NMR
(CDCl3, 100 MHz): 152.2, 147.0, 136.4, 133.9, 131.8, 130.6, 129.6,
128.6, 128.3, 128.2, 127.2, 126.7, 126.3, 123.3, 122.8, 116.9, 101.3,
21.1, 18.4. FTIR: 3045, 2918, 1602, 1357, 1270, 1384, 1032, 826,
752, 694 cm-1; HRMS (ESI-TOF) m/z calculated for C21H19N2Se+
379.0708 (M+H)+, found 379.0711.
Following the general procedure, isolated yield (108.1 mg, 87%) as a
1
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.20-8.10 (m,
3H), 8.11-8.06 (m, 1H), 7.86 (dd, J=7.8, 1.6 Hz, 1H), 7.72-7.50 (m,
4H), 7.44-7.30 (m, 3H), 7.19-7.09 (m, 2H), 6.85 (dd, J=7.3, 1.1 Hz,
1H), 2.24 (s, 3H). 13C-NMR (CDCl3, 100 MHz): 152.4, 147.2, 134.3,
133.9, 132.2, 129.7, 129.6, 128.8, 128.7, 128.4, 128.3, 127.0, 126.6,
126.5, 126.4, 125.2, 125.1, 123.4, 122.9, 116.9, 100.9, 18.4. FTIR:
3045, 1820, 1501, 1371, 1242, 1064, 769, 685, 602 cm-1; HRMS
(ESI-TOF) m/z calculated for C24H19N2Se+ 415.0708 (M+H)+, found
415.0710.
3-((3-Chlorophenyl)selanyl)-6-methyl-2-phenylimidazo[1,2-
a]pyridine (2o)
Following the general procedure, isolated yield (87.2 mg, 73%) as a
1
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.17-8.05 (m,
3-((4-Chlorophenyl)selanyl)-2-phenylimidazo[1,2-a]pyridine (2i)
Following the general procedure, isolated yield (92.2 mg, 80%) as a
colorless oil; 1H-NMR (400 MHz, Chloroform-d) δ 8.36-8.27 (m,
1H), 8.16-8.06 (m, 2H), 7.77-7.69 (m, 1H), 7.47-7.41 (m, 2H), 7.41-
7.37 (m, 1H), 7.37-7.29 (m, 1H), 7.18-7.10 (m, 2H), 7.06-6.97 (m,
2H), 6.88 (td, J=6.8, 1.2 Hz, 1H). 13C-NMR (CDCl3, 100 MHz):
152.0, 147.8, 133.6, 132.9, 129.8, 129.5, 129.1, 128.7, 128.6, 128.4,
126.6, 125.4, 117.7, 113.2, 102.4. FTIR: 2363, 1629, 1490, 1470,
1340, 1224, 1058, 838, 687 cm-1; HRMS (ESI-TOF) m/z calculated
for C19H14ClN2Se+ 385.0005 (M+H)+, found 385.0002.
3H), 7.65 (d, J=9.1 Hz, 1H), 7.49-7.34 (m, 3H), 7.23-7.05 (m, 4H),
6.98-6.89 (m, 1H), 2.32 (d, J=1.1 Hz, 3H). 13C-NMR (CDCl3, 100
MHz,): 152.0, 147.0, 135.5, 133.7, 133.2, 130.6, 130.0, 128.6, 128.5,
128.3, 127.6, 126.8, 125.9, 123.1 (2C), 117.0, 101.5, 18.4. FTIR:
3055, 2915, 1573, 1458, 1329, 1246, 1026, 814, 766 cm-1; HRMS
(ESI-TOF) m/z calculated for C20H16ClN2Se+ 399.0162 (M+H)+,
found 399.0165.
3-(Butylselanyl)-6-methyl-2-phenylimidazo[1,2-a]pyridine (3a)
Following the general procedure, isolated yield (92.9 mg, 90%) as a
1
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.26-8.23 (m,
3-((4-Bromophenyl)selanyl)-6-methyl-2-phenylimidazo[1,2-
a]pyridine (2j)
1H), 8.19-8.08 (m, 2H), 7.48 (dd, J=9.1, 0.9 Hz, 1H), 7.40-7.35 (m,
2H), 7.32-7.25 (m, 1H), 7.04 (dd, J=9.0, 1.7 Hz, 1H), 2.58 (t, J=7.3
Hz, 2H), 2.32 (d, J=1.1 Hz, 3H), 1.44-1.34 (m, 2H), 1.25-1.19 (m,
2H), 0.68 (t, J=7.3 Hz, 3H). 13C-NMR (CDCl3, 100 MHz): 150.1,
146.2, 134.4, 128.8, 128.6, 128.1, 127.9, 123.3, 122.3, 116.8, 103.8,
32.0, 29.1, 22.7, 18.5, 13.4. FTIR: 2957, 2926, 2870, 1536, 1462,
1337, 1244, 801, 772 cm-1; HRMS (ESI-TOF) m/z calculated for
C18H21N2Se+ 345.0864 (M+H)+, found 345.0866.
Following the general procedure, isolated yield (107.4 mg, 81%) as a
1
colorless oil; H-NMR (400 MHz, Chloroform-d) δ 8.05-8.01 (m,
2H), 7.55 (dd, J=9.1, 0.9 Hz, 1H), 7.48-7.26 (m, 4H), 7.26-7.20 (m,
2H), 7.07 (ddd, J=26.6, 9.1, 1.7 Hz, 1H), 6.93-6.83 (m, 2H), 2.26 (s,
3H). 13C-NMR (CDCl3, 100 MHz): 151.9, 146.9, 133.7, 132.7, 130.3,
129.8, 129.6, 128.6, 128.5, 128.3, 123.1, 123.0, 120.6, 117.0, 101.7,
18.4. FTIR: 2922, 1504, 1477, 1462, 1337, 1242, 1068, 803, 691
3-(Butylselanyl)-8-methyl-2-phenylimidazo[1,2-a]pyridine (3b)