Paper
NJC
+
(
d, J = 6.8 Hz, 1H, Ar-H), 8.27 (s, 1H, triazole-CH), 8.20 (m, 2H, (2C), 113.8, 61.9, 60.8, 56.5, 50.4; ESI-MS (m/z) = 494.1 [M + H] ;
2 22 3 5 2
Ar-H), 7.64 (m, 3H, Ar-H), 7.51 (m, 2H, CH ), 7.32 (m, 1H, Ar-H), anal. calcd for C26H F N O ; C, 63.28; H, 4.49; N, 14.19. Found:
6
.97 (m, 3H, Ar-H), 5.78 (s, 2H, CH ), 4.91 (s, 2H, CH ), 4.72 C, 63.20; H, 4.47; N, 14.31.
2
2
1
3
(s, 2H, CH ), 3.76 (s, 3H, CH ); C-NMR (CDCl , 100 MHz,
2 3 3
4.1.11.6. 2-(4-Methoxyphenyl)-3-(((1-(4-methoxybenzyl)-1H-1,2,3-
d in ppm): 161.7, 149.2, 148.8, 142.3, 140.4, 132.6 (2C), 131.5,
triazol-4-yl)methoxy) methyl)imidazo[1,2-a]pyridine (13f). Yield: 90%;
1
1
4
30.0 (2C), 127.7 (2C), 126.9, 126.3, 120.5, 120.1, 119.6, 118.0,
1
H-NMR (DMSO-d
(s, 1H, triazole-CH), 7.65 (d, J = 8.0 Hz, 2H, Ar-H), 7.58 (d, J = 8.8 Hz,
H, Ar-H), 7.29 (m, 1H, Ar-H), 7.19 (m, 4H, Ar-H), 6.77 (m, 3H, Ar-H),
.53 (s, 2H, CH ), 4.91 (s, 2H, CH ), 4.65 (s, 2H, CH ), 3.83 (s, 3H, CH ),
3.79 (s, 3H, CH ); C-NMR (CDCl , 100 MHz, d in ppm): 161.8, 158.2,
triazol-4-yl)methoxy) methyl)imidazo[1,2-a]pyridine (13b). Yield: 149.2, 148.9, 140.6, 130.8 (2C), 130.0, 129.1 (2C), 127.9, 127.1, 126.5,
6
, 400 MHz, d in ppm): 8.38 (m, 1H, Ar-H), 8.13
14.9 (2C), 113.7, 112.8, 61.9, 60.7, 56.6, 50.5; ESI-MS (m/z) =
+
51.1 [M + H] ; anal. calcd for C26
22 6 2
H N O ; C, 69.32; H, 4.92;
1
N, 18.66. Found: C, 69.31; H, 4.93; N, 18.67.
5
2
2
2
3
13
4.1.11.2. 2-(4-Methoxyphenyl)-3-(((1-(4-methylbenzyl)-1H-1,2,3-
3
3
1
9
2%; H-NMR (DMSO-d , 400 MHz, d in ppm): 8.390 (m, 1H, 120.6, 120.0, 118.3, 115.5 (2C), 114.8 (2C), 113.6, 61.9, 60.8, 56.8, 56.0,
6
+
Ar-H), 8.13 (s, 1H, triazole-CH), 7.65 (d, J = 8.4 Hz, 2H, Ar-H), 7.59 50.4; ESI-MS (m/z) = 456.1 [M + H] ; anal. calcd for C26
25 5 3
H N O ;
(
d, J = 9.2 Hz, 1H, Ar-H), 7.31 (t, J = 14.8 Hz, 1H, Ar-H), 7.19 (m, C, 68.56; H, 5.53; N, 15.37. Found: C, 68.61; H, 5.57; N, 15.41.
4
4
H, Ar-H), 6.98 (m, 3H, Ar-H), 5.52 (s, 2H, CH
.68 (s, 2H, CH ), 3.78 (s, 3H, CH ), 2.25 (s, 3H, CH
, 100 MHz, d in ppm): 161.5, 149.3, 148.9, 140.9, 137.0,
2
), 4.90 (s, 2H, CH
2
),
1
3
4.1.11.7. 3-(((1-(4-Chlorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)-
-(4-methoxy phenyl)imidazo[1,2-a]pyridine (13g). Yield: 88%; H-NMR
2
3
3
); C-NMR
1
2
(
(
(CDCl
3
DMSO-d , 400 MHz, d in ppm): 8.41 (d, J = 6.8 Hz, 1H, Ar-H), 8.24
6
1
1
33.5, 130.6, 129.8 (2C), 129.4 (2C), 127.3 (2C), 126.7, 126.0,
s, 1H, triazole-CH), 8.20 (d, J = 6.8 Hz, 1H, Ar-H), 7.63 (m, 3H, Ar-H),
7.51 (m, 2H, CH ), 7.31 (t, J = 12.0 Hz, 2H, Ar-H), 6.96 (m, 3H, Ar-H),
.78 (s, 2H, CH ), 4.91 (s, 2H, CH ), 4.72 (s, 2H, CH ), 3.75 (s, 3H,
); C-NMR (CDCl , 100 MHz, d in ppm): 161.7, 149.1, 148.9,
140.5, 135.1, 132.6, 130.0, 129.4 (2C), 127.8 (2C), 127.7 (2C), 126.9,
-yl)methoxy)methyl) imidazo[1,2-a]pyridine (13c). Yield: 89%; H-NMR 126.5, 120.7, 120.2, 118.1, 114.9 (2C), 113.8, 61.7, 60.8, 56.5, 50.6;
20.7, 120.1, 118.0, 114.8 (2C), 113.5, 61.9, 60.8, 56.5, 50.7, 21.5;
+
2
ESI-MS (m/z) = 440.1 [M + H] ; anal. calcd for C H N O ; C,
7
2
6
25 5 2
5
2
2
2
1.05; H, 5.73; N, 15.93. Found: C, 71.05; H, 5.75; N, 15.96.
13
CH
3
3
4
.1.11.3. 2-(4-Methoxyphenyl)-3-(((1-(4-nitrobenzyl)-1H-1,2,3-triazol-
1
4
+
(DMSO-d
6
5 2
, 400 MHz, d in ppm): 8.69 (d, J = 6.8 Hz, 1H, Ar-H), 8.35 (s, ESI-MS (m/z) = 460.1 [M + H] ; anal. calcd for C25H22ClN O ; 65.29;
1
H, triazole-CH), 8.30 (m, 2H, Ar-H), 7.75 (m, 3H, Ar-H), 7.59 (m, 2H, H, 4.82; N, 15.23. Found: C, 65.27; H, 4.81; N, 15.20.
CH
s, 2H, CH
00 MHz, d in ppm): 161.8, 149.2, 148.9, 145.7, 141.1, 140.5, 130.1,
29.6 (2C), 127.8 (2C), 126.9, 126.2, 124.3 (2C), 120.5, 120.0, 118.5,
2
), 7.40 (m, 1H, Ar-H), 7.10 (m, 3H, Ar-H), 5.80 (s, 2H, CH
2
), 4.98
13
4.1.11.8. 3-(((1-(2-Fluorobenzyl)-1H-1,2,3-triazol-4-yl)methoxy)methyl)-
-(4-methoxy phenyl)imidazo[1,2-a]pyridine (13h). Yield: 85%;
(
1
1
2
), 4.78 (s, 2H, CH
2
3
), 3.79 (s, 3H, CH ); C-NMR (CDCl
3
,
2
1
H-NMR (DMSO-d
6
, 400 MHz, d in ppm): 8.40 (d, J = 6.4 Hz,
+
1H, Ar-H), 8.25 (s, 1H, triazole-CH), 8.11 (m, 2H, Ar-H), 7.55
114.6 (2C), 113.7, 61.8, 60.7, 56.5, 50.4; ESI-MS (m/z) = 471.1 [M + H] ;
(
(
m, 3H, Ar-H), 7.38 (m, 2H, CH
2
), 7.26 (m, 1H, Ar-H), 6.86
anal. calcd for C H N O ; C, 63.82; H, 4.71; N, 17.86. Found: C,
25 22 6 4
m, 3H, Ar-H), 5.78 (s, 2H, CH ), 4.91 (s, 2H, CH ), 4.72 (s, 2H,
2
2
63.85; H, 4.73; N, 17.91.
1
3
CH ), 3.76 (s, 3H, CH ); C-NMR (CDCl , 100 MHz, d in ppm):
2
3
3
1
1
1
62.4, 161.9, 149.1, 148.9, 140.5, 131.6, 130.1, 128.4 (2C), 127.8,
26.8, 126.4, 125.5, 124.8, 120.6, 120.1, 118.0, 116.2, 114.8 (2C),
13.9, 61.8, 60.5, 56.7, 50.4; ESI-MS (m/z) = 444.1 [M + H] ; anal.
4
.1.11.4. 2-(4-Methoxyphenyl)-3-(((1-(4-fluorobenzyl)-1H-1,2,3-
triazol-4-yl)methoxy)methyl) imidazo[1,2-a]pyridine (13d). Yield:
+
1
9
6
2
0%; H-NMR (DMSO-d
.4 Hz, 1H, Ar-H), 8.23 (s, 1H, triazole-CH), 8.20 (d, J = 7.2 Hz,
H, Ar-H), 7.63 (m, 3H, Ar-H), 7.50 (m, 2H, CH ), 7.30 (t, J = 12.4
), 4.90 (s, 2H,
CH ), 4.72 (s, 2H, CH ), 3.76 (s, 3H, CH ); C-NMR (CDCl3,
6
, 400 MHz, d in ppm): 8.41 (d, J =
calcd for C25
C, 67.75; H, 5.03; N, 15.81.
5 2
H22FN O ; C, 67.71; H, 5.00; N, 15.79. Found:
2
Hz, 1H, Ar-H), 6.96 (m, 3H, Ar-H), 5.77 (s, 2H, CH
2
4.1.11.9. 3-(((1-(4-Fluoro-2-methylbenzyl)-1H-1,2,3-triazol-4-yl)-
1
3
2
2
3
methoxy)methyl)-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine (13i).
Yield: 88%; H-NMR (DMSO-d , 400 MHz, d in ppm): 8.29
1
1
1
00 MHz, d in ppm): 161.8, 160.6, 149.2, 148.9, 140.2, 132.5,
30.2 (2C), 128.7 (2C), 127.8, 126.9, 126.5, 120.8, 120.0, 118.6,
16.1 (2C), 114.9 (2C), 113.8, 61.8, 60.5, 56.6, 50.4; ESI-MS
m/z) = 444.1 [M + H] ; anal. calcd for C25
1
6
(
m, 1H, Ar-H), 8.25 (s, 1H, triazole-CH), 8.19 (d, J = 5.2 Hz, 2H,
Ar-H), 7.59 (m, 2H, Ar-H), 7.36 (m, 2H, CH ), 7.29 (m, 1H, Ar-H),
.87 (m, 3H, Ar-H), 5.77 (s, 2H, CH ), 4.91 (s, 2H, CH ), 4.73
s, 2H, CH ), 3.76 (s, 3H, CH ), 2.36 (s, 3H, CH
CDCl , 100 MHz, d in ppm): 161.8, 160.5, 149.2, 148.9, 140.3,
39.6, 133.8, 131.3, 127.8 (2C), 126.9, 126.2, 120.6, 120.0, 118.4,
116.5, 114.8 (2C), 113.7, 113.0, 112.8, 61.9, 60.8, 56.6, 50.4, 19.4;
+
2
(
H
22FN
5
O
2
; C, 67.71;
6
(
(
2
2
H, 5.00; N, 15.79. Found: C, 67.74; H, 5.01; N, 15.75.
1
3
2
3
3
); C-NMR
4
.1.11.5. 2-(4-Methoxyphenyl)-3-(((1-(4-(trifluoromethyl)benzyl)-
H-1,2,3-triazol-4-yl) methoxy)methyl)imidazo[1,2-a]pyridine (13e).
3
1
1
1
Yield: 92%; H-NMR (DMSO-d
6
, 400 MHz, d in ppm): 8.43 (d, J =
.4 Hz, 1H, Ar-H), 8.26 (s, 1H, triazole-CH), 8.19 (m, 2H, Ar-H),
.63 (m, 3H, Ar-H), 7.49 (m, 2H, CH ), 7.31 (m, 1H, Ar-H), 6.95
+
ESI-MS (m/z) = 458.1 [M + H] ; anal. calcd for C H FN O ;
C, 68.26; H, 5.29; N, 15.31. Found: C, 68.25; H, 5.26; N, 15.30.
6
7
26 24
5 2
2
(
m, 3H, Ar-H), 5.78 (s, 2H, CH ), 4.90 (s, 2H, CH ), 4.72 (s, 2H,
2
2
1
3
CH
2 3 3
), 3.76 (s, 3H, CH ); C-NMR (CDCl , 100 MHz, d in ppm):
Conflicts of interest
1
1
61.7, 149.3, 148.9, 141.4, 140.5, 131.6, 130.1, 129.1 (2C), 128.4,
27.8 (2C), 126.9, 126.5 (2C), 126.4, 120.6, 120.2, 118.1, 114.9 There are no conflicts to declare.
16298 | New J. Chem., 2019, 43, 16281--16299 This journal is ©The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019