EBENEZER Et al.
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(3″/6″), 127.8 (C‐2″/6″), 126.9 (C‐12), 126.7 (C‐4′), 125.8
(C‐8d), 123.9 (C‐10), 119.9 (C‐8a), 119.2 (C‐2′/6′), 116.6
(C‐11), 113.5 (C‐4), 113.2 (C‐13), 29.4 (C‐8); HRMS (pos)
[M + H] 427.1923 [calcd forC29H22N4 427.1923].
(C‐7), 135.0 (C‐1″), 129.5 (d, J = 8.2 Hz,C‐2″/6″), 129.5
(C‐5/3′/5′), 128.8 (C‐8b/8f), 127.9 (d, J = 18.5 Hz, C‐3″/5″),
127.7 (C‐8c/8e), 126.7 (C‐12), 126.0 (C‐4′), 124.3 (C‐8d),
123.7 (C‐10), 119.7 (C‐8a), 119.1 (C‐2′/6′), 117.5 (C‐11),
115.4 (C‐4) 112.3 (C‐13), 29.6 (C‐8); HRMS (pos) [M + H]
445.1833 [calcd for C29H22FN4, 445.1829].
3‐Benzyl‐2‐(3‐(3,4‐dimethoxyphenyl)‐1‐phenyl‐1H‐
pyrazol‐4‐yl)imidazo[1,2‐α]pyridine8b
Yellow oil; Yield: 66%; IR vmax 3,287, 3,112, 2,925, 2,853,
2,033, 1,598, 1,774, 1,671 cm−1; 1H NMR (400 MHz,
CDCl3): δ8.12 (1H, s, H‐5), 7.76 (2H, d, J = 7.6 Hz, H‐2′/6′),
7.66 (2H, t, J = 6.8 Hz, H‐12/10), 7.45 (3H, t, J = 7.6 Hz,
H‐3′/5′,6″), 7.35 (1H, d, J = 1.2 Hz, H‐2″), 7.28 (1H, t,
J = 7.6 Hz, H‐4′), 7.20 (5H, m, H‐8d, 8c/8e, 8b/8f), 6.88 (1H,
dd, J = 7.8, 1.8 Hz, H‐13), 6.72 (1H, d, J = 8.0 Hz, H‐5″),
6.68 (1H, t, J = 7.8 Hz, H‐11), 3.71 (3H, s, H‐4a), 4.01( 2H,
s, H‐8), 3.82 (3H, s, H‐3a); 13C NMR (100 MHz, CDCl3):
δC151.4 (C‐3), 148.9 (C‐6), 144.8 (C‐14), 144.8 (C‐1′), 139.9
(C‐7), 136.7 (C‐1a), 129.4 (C‐5/3′/5′), 128.7 (C‐8b/8f), 127.8
(C‐8c/8e), 126.7 (C‐12), 126.5 (C‐4′), 126.1 (C‐1″), 124.1
(C‐8d), 123.6 (C‐10), 120.5 (C‐6″), 119.1 (C‐2′/6′), 118.7
(C‐8a), 117.4 (C‐11), 115.1 (C‐4), 112.2 (C‐13), 111.2 (C‐2″),
111.0 (C‐5″), 55.8 (C‐3a), 55.7 (C‐4a), 29.6 (C‐8); HRMS
(pos) [M + H] 487.2142 [calcd for C31H27N4O2 487.2134].
3‐Benzyl‐2‐(3‐(2‐hydroxylphenyl)‐1‐phenyl‐1H‐
pyrazol‐4‐yl)imidazo[1,2‐α]pyridine8e
Yellowish solid powder; mp 163–165°C; Yield: 68%; IR
vmax 3,050, 2,924, 2,854, 2,531, 1,941, 1,688, 1,597, 1,493;
1H NMR (400 MHz, CDCl3): δ8.31 (1H, s, H‐5), 7.99 (2H,
d, J = 4.6 Hz, H‐2a), 7.78 (2H, d, J = 7.6 Hz, H‐2′/6′), 7.58
(1H, d, J = 9.0 Hz, H‐10), 7.42–7.51 (4H, m, H‐3′, 3″, 5′, 12),
7.27 (1H, t, J = 7.4 Hz, H‐4′), 7.18 (1H, td, J = 7.6, 1.6 Hz,
H‐8d), 7.08–7.13 (5H, m, H‐4″, 8b, 8f, 8c, 8e), 6.75–6.78
(2H, m, H‐13,5″), 6.60 (1H, t, J = 0.7 Hz, H‐11), 6.47 (1H,
d, J = 8.2 Hz, H‐6″), 3.95 (2H, s, H‐8); 13C NMR (100 MHz,
CDCl3) δC156.1 (C‐2″), 150.1 (C‐3), 144.8 (C‐6), 139.1 (C‐14),
139.1 (C‐1′), 136.5 (C‐7), 129.7 (C‐5), 129.6 (C‐3′/5′), 128.9
(C‐8b/8f), 128.6 (C‐8c/8e), 127.8 (C‐4″/6″), 127.0 (C‐12),
126.9 (C‐4′), 124.5 (C‐8d), 123.7 (C‐10), 120.1 (C‐8a), 119.4
(C‐5″), 119.0 (C‐2′/6′), 118.1 (C‐1″), 117.9 (C‐11), 117.6
(C‐3″), 115.2 (C‐4), 112.5 (C‐13), 29.7 (C‐8); HRMS (pos)
[M + H] 443.1875 [calcd for C29H23N4O 443.1872].
3‐Benzyl‐2‐(3‐(2‐fluorophenyl)‐1‐phenyl‐1H‐pyrazol‐4‐
yl)imidazo[1,2‐α]pyridine8c
Brown oil; Yield: 65%; IR vmax 3,649, 3,024, 2,548, 1,929,
3‐Benzyl‐2‐(3‐(2‐methoxyphenyl)‐1‐phenyl‐1H‐pyrazol‐4‐
yl)imidazo[1,2‐α]pyridine8f
1,794, 1,596, 1,494 cm−1; H NMR (400 MHz, CDCl3): δ
1
8.18 (1H, s, H‐5), 7.70 (2H, d, J = 7.9 Hz, H‐2′/6′), 7.51 (3H,
m, H‐10,3″,12), 7.36 (2H, t, J = 7.9 Hz, H‐3′/5′), 7.22 (1H,
t, J = 7.9 Hz, H‐4′), 6.95–7.15 (6H, m, H‐5″/8b/8f/8c/8e/8d),
6.87 (1H, t, J = 8.2 Hz, H‐4″), 6.76–6.80 (2H, m, H‐6″/13),
6.56 (1H, t, J = 7.8 Hz, H‐11), 3.95 (2H, s, H‐8); 13C NMR
(400 MHz, CDCl3): δC161.4 (d, J = 248.6 Hz, C‐2″),
158.9 (C‐3), 147.0 (C‐6), 144.8 (C‐14), 139.9 (C‐1′), 136.4
(C‐7), 131.6 (d, J = 3.0 Hz, C‐6″), 129.9 (d, J = 7.8 Hz,
C‐4″), 129.5 (C‐3′/5′), 128.7 (C‐8b/8f), 128.0 (C‐5), 127.7
(C‐8c/8e), 126.7 (C‐12), 126.6 (C‐4′), 124.1 (C‐5″), 124.0
(C‐8d), 123.6 (C‐10), 121.5 (d, J = 14.5 Hz, C‐1″), 119.2
(C‐2′/6′), 118.8 (C‐8a), 117.3 (C‐11), 117.3 (C‐4), 115.9 (d,
J = 21.6 Hz, C‐3″), 112.0 (C‐13), 29.4 (C‐8); HRMS (pos)
[M + H] 445.1831 [calcd for C29H21FN4, 445.1829].
Brownish solid powder; mp 158–160°C; Yield: 68%; IR vmax
1
3,362, 3,052, 2,923, 2,852, 1,941, 1,658, 1,598, 1,494; H
NMR (400 MHz, CDCl3): δ8.31 (1H, s, H‐5), 7.78 (1H, d,
J = 8.0 Hz, H‐2′/6′), 7.61 (1H, d, J = 8.9 Hz, H‐10), 7.52
(1H, d, J = 6.8 Hz, H‐6″), 7.45 (2H, t, J = 8.4 Hz H‐3′/5′),
7.42 (1H, d, J = 8.0 Hz, H‐12), 7.27 (1H, d, J = 7.4 Hz, H‐8d),
7.21 (1H, t, J = 8.5 Hz, H‐4′), 7.10 (4H, m, H‐8b/8f,8c/8e),
6.90 (1H, t, J = 7.4 Hz, H‐4″), 6.76–6.78 (2H, m, H‐13,5″),
6.65 (1H, d, J = 8.3 Hz, H‐3″), 6.61 (1H, t, J = 6.7 Hz,
H‐11), 3.92 (2H, s, H‐8), 3.37 (3H, s, H‐2a); 13C NMR
(100 MHz, CDCl3): δC157.4 (C‐2″), 149.4 (C‐3), 144.4
(C‐6), 137.4 (C‐14), 140.1 (C‐1′), 136.6 (C‐7), 131.6 (C‐6″),
129.7 (C‐5), 129.4 (C‐3′/5′), 128.6 (C‐8b/8f), 127.7 (C‐4″),
127.7 (C‐8c/8e), 126.4 (C‐12), 126.4 (C‐4′), 123.8 (C‐8d),
123.5 (C‐5″), 122.8 (C‐1″), 120.7 (C‐10), 119.2 (C‐2′/6′),
118.6 (C‐8a), 117.2 (C‐11), 112.3 (C‐4), 111.9 (C‐3″),
111.3 (C‐13), 55.3 (C‐2a), 29.2 (C‐8);HRMS (pos) [M + H]
457.2041 [calcd for C30H25N4O, 457.2028].
3‐Benzyl‐2‐(3‐(4‐fluorophenyl)‐1‐phenyl‐1H‐pyrazol‐4‐
yl)imidazo[1,2‐α]pyridine8d
Dark brown oil; Yield: 62%; IR vmax 3,024, 2,925, 1,929,
1
1,794, 1,596, 1,494; H NMR (400 MHz, CDCl3): δ8.32
(1H, s, H‐5), 7.79 (2H, d, J = 7.9 Hz, H‐2′/6′), 7.61 (1H, d,
J = 9.1 Hz, H‐10), 7.40–7.51 (5H, m, H‐3′/5′, 2″/6″, 12), 7.29
(1H, t, J = 7.0 Hz, H‐4′), 7.09–7.14 (7H, m, H‐3″/5″, 8b/8f,
8c/8e, 8d), 6.75–6.78 (1H, m, H‐13), 6.62 (1H, t, J = 6.7 Hz,
H‐11), 3.95 (2H, s, H‐8); 13C NMR (100 MHz, CDCl3):
δC149.6 (C‐3), 145.0 (C‐6), 139.8 (C‐14), 136.4 (C‐1′), 136.2
3‐benzyl‐2‐(3‐(4‐methoxyphenyl)‐1‐phenyl‐1H‐pyrazol‐4‐
yl)imidazo[1,2‐α]pyridine8g
Brown oil; Yield: 70%; IR vmax 3,361, 3,058, 2,924, 2,548,
1,679, 1,597, 1,495 cm−1; 1H NMR (400 MHz, CDCl3): δ8.20
(1H, s, H‐5), 7.81 (3H, d, J = 8.7 Hz, H‐2′/6′,10), 7.67–7.70
(1H, m, H‐12), 7.64 (d, J = 8.8 Hz, H‐2″/6″), 7.47 (2H, t,