G
Synthesis
H. Yu et al.
Paper
1
H NMR (CDCl , 600 MHz): = 7.96 (d, J = 7.5 Hz, 2 H), 7.49 (d, J = 7.7
1-Benzyl-3-(1,3-diphenyl-1H-pyrazol-5-yl)-1H-indole (3o)
3
Hz, 2 H), 7.46 (d, J = 8.2 Hz, 1 H), 7.43 (t, J = 7.5 Hz, 2 H), 7.33 (t, J = 7.6
Hz, 3 H), 7.29 (d, J = 7.0 Hz, 1 H), 7.12 (s, 1 H), 6.96 (d, J = 8.1 Hz, 1 H),
White solid; yield: 97.8 mg (92%); mp 175–176 °C.
1
H NMR (CDCl , 600 MHz): = 7.96 (d, J = 7.7 Hz, 2 H), 7.67 (d, J = 7.9
3
6.90 (s, 1 H), 6.65 (s, 1 H), 3.67 (s, 3 H), 2.49 (s, 3 H).
Hz, 1 H), 7.44 (d, J = 8.0 Hz, 2 H), 7.41 (d, J = 7.3 Hz, 1 H), 7.31 (t, J = 7.4
Hz, 1 H), 7.29–7.24 (m, 8 H), 7.20 (t, J = 7.9 Hz, 1 H), 7.14 (t, J = 7.7 Hz,
13
C NMR (CDCl , 150 MHz): = 152.0, 140.7, 138.7, 137.1, 133.4,
3
132.2, 128.8 (2 C), 128.6 (2 C), 127.8, 127.7, 127.3, 125.8 (2 C), 125.4
1
H), 6.98 (d, J = 7.0 Hz, 2 H), 6.95 (s, 1 H), 6.72 (s, 1 H), 5.15 (s, 2 H).
(2 C), 124.4, 122.0, 119.7, 109.4, 104.9, 104.5, 32.9, 21.8.
13
C NMR (CDCl , 150 MHz): = 152.0, 140.5, 138.3, 136.6, 136.1,
3
HRMS: m/z [M + H] calcd for C 5H22N3+: 364.1808; found: 364.1814.
+
2
133.3, 128.8 (2 C), 128.7 (2 C), 128.6 (2 C), 127.8 (2 C), 127.7, 127.4,
26.8, 126.7 (2 C), 125.8 (2 C), 125.4 (2 C), 122.5, 120.5, 120.0, 110.0,
105.5, 104.5, 50.1.
1
3-(1,3-Diphenyl-1H-pyrazol-5-yl)-1,7-dimethyl-1H-indole (3k)
HRMS: m/z [M + H] calcd for C30H24N3+: 426.1965; found: 426.1961.
+
White solid; yield: 79.9 mg (88%); mp 155–156 °C.
1
H NMR (CDCl , 600 MHz): = 7.95 (d, J = 7.2 Hz, 2 H), 7.46 (t, J = 7.9
3
Hz, 3 H), 7.42 (d, J = 7.9 Hz, 2 H), 7.34–7.31 (m, 3 H), 7.27 (d, J = 7.3 Hz,
1-Methyl-3-[3-phenyl-1-(p-tolyl)-1H-pyrazol-5-yl]-1H-indole (3p)
1
H), 6.99 (t, J = 7.7 Hz, 1 H), 6.94 (d, J = 7.0 Hz, 1 H), 6.89 (s, 1 H), 6.59
White solid; yield: 82.6 mg (91%); mp 133–134 °C.
(s, 1 H), 3.94 (s, 3 H), 2.75 (s, 3 H).
1
H NMR (CDCl , 600 MHz): = 7.95 (d, J = 8.3 Hz, 2 H), 7.62 (d, J = 8.0
3
13
C NMR (CDCl , 150 MHz): = 152.0, 140.6, 138.4, 135.4, 133.4,
3
Hz, 1 H), 7.41 (t, J = 7.9 Hz, 2 H), 7.34 (d, J = 8.3 Hz, 2 H), 7.32 (d, J = 7.3
Hz, 1 H), 7.29 (d, J = 8.0 Hz, 1 H), 7.25 (t, J = 7.3 Hz, 1 H), 7.13 (t, J = 7.9
Hz, 1 H), 7.11 (d, J = 8.1 Hz, 2 H), 6.90 (s, 1 H), 6.69 (s, 1 H), 3.66 (s, 3
H), 2.33 (s, 3 H).
129.4, 128.8 (2 C), 128.6 (2 C), 127.8, 127.7, 127.3, 125.8 (2 C), 125.2
(2 C), 125.0, 121.4, 120.5, 118.1, 104.8 (2 C), 37.0, 19.7.
HRMS: m/z [M + H] calcd for C25H22N3+: 364.1808; found: 364.1805.
+
13
C NMR (CDCl , 150 MHz): = 151.8, 138.4, 138.2, 137.2, 136.6,
3
3
-(1,3-Diphenyl-1H-pyrazol-5-yl)-5-methoxy-1-methyl-1H-indole
133.4, 129.4 (2 C), 128.5 (2 C), 128.2, 127.7, 126.5, 125.8 (2 C), 125.2
(2 C), 122.2, 120.2, 120.0, 109.4, 105.1, 104.3, 32.9, 21.1.
(3l)
HRMS: m/z [M + H] calcd for C25H22N3+: 364.1808; found: 364.1800.
+
White solid; yield: 87.2 mg (92%); mp 155–156 °C.
1
H NMR (CDCl , 600 MHz): = 7.96 (d, J = 7.7 Hz, 2 H), 7.50 (t, J = 7.8
3
Hz, 2 H), 7.44 (t, J = 7.7 Hz, 2 H), 7.34 (d, J = 7.5 Hz, 1 H), 7.33 (t, J = 7.9
Hz, 2 H), 7.27 (d, J = 7.4 Hz, 1 H), 7.19 (d, J = 8.8 Hz, 1 H), 6.88 (dd, J =
3-[1-(4-Chlorophenyl)-3-phenyl-1H-pyrazol-5-yl]-1-methyl-1H-
indole (3q)
8
3
.8, 2.2 Hz, 1 H), 6.85 (s, 1 H), 6.83 (s, 1 H), 6.82 (s, 1 H), 3.70 (s, 3 H),
.67 (s, 3 H).
White solid; yield: 87.1 mg (91%); mp 125–126 °C.
1
H NMR (CDCl , 600 MHz): = 7.93 (d, J = 7.4 Hz, 2 H), 7.62 (d, J = 7.9
3
13
C NMR (CDCl , 150 MHz): = 154.6, 152.0, 140.8, 138.8, 133.3,
3
Hz, 1 H), 7.43 (t, J = 7.3 Hz, 4 H), 7.35–7.33 (m, 2 H), 7.29–7.26 (m, 3
H), 7.13 (t, J = 7.4 Hz, 1 H), 6.90 (s, 1 H), 6.80 (s, 1 H), 3.75 (s, 3 H).
1
1
32.0, 128.9 (2 C), 128.7, 128.6 (2 C), 127.9, 127.2, 126.6, 125.8 (2 C),
25.0 (2 C), 112.8, 110.3, 104.7, 104.6, 101.3, 55.7, 33.1.
13
C NMR (CDCl , 150 MHz): = 152.3, 139.2, 138.5, 136.7, 133.1,
3
+
+
HRMS: m/z [M + H] calcd for C 5H N O : 380.1757; found: 380.1752.
2
22
3
132.8, 128.9 (2 C), 128.6 (2 C), 128.3, 128.0, 126.4, 126.2 (2 C), 125.8
2 C), 122.5, 120.4, 119.9, 109.6, 105.2, 104.8, 33.0.
(
5-Bromo-3-(1,3-diphenyl-1H-pyrazol-5-yl)-1-methyl-1H-indole(3m)
H]+ calcd for C24H19ClN3+: 384.1262; found:
HRMS: m/z [M
+
White solid; yield: 99.3 mg (93%); mp 150–151 °C.
384.1260.
1
H NMR (CDCl , 600 MHz): = 7.94 (d, J = 7.3 Hz, 2 H), 7.66 (s, 1 H),
3
7.42 (t, J = 7.9 Hz, 4 H), 7.34–7.29 (m, 5 H), 7.13 (d, J = 8.6 Hz, 1 H),
3-(1-Ethyl-3-phenyl-1H-pyrazol-5-yl)-1-methyl-1H-indole (3r)
6
.87 (s, 1 H), 6.69 (s, 1 H), 3.63 (s, 3 H).
Colorless oil; yield: 67.7 mg (90%).
13
C NMR (CDCl , 150 MHz): = 152.1, 140.4, 137.7, 135.3, 133.2,
1
3
H NMR (CDCl , 600 MHz): = 7.88 (d, J = 8.3 Hz, 2 H), 7.64 (d, J = 7.9
3
129.3, 128.8 (2 C), 128.6 (2 C), 128.0, 127.9, 127.5, 125.8 (2 C), 125.3
Hz, 1 H), 7.40 (t, J = 7.6 Hz, 2 H), 7.37 (d, J = 8.3 Hz, 1 H), 7.32–7.29 (m,
H), 7.20 (t, J = 7.9 Hz, 1 H), 7.13 (s, 1 H), 6.65 (s, 1 H), 4.24–4.21 (m, 2
(2 C), 125.2, 122.5, 113.7, 111.0, 104.7, 104.6, 33.1.
2
HRMS: m/z [M
+
H]+ calcd for C24H19BrN3+: 428.0757; found:
H), 3.83 (s, 3 H), 1.44 (t, J = 7.2 Hz, 3 H).
428.0762.
13
C NMR (CDCl , 150 MHz): = 150.6, 137.6, 136.7, 133.9, 128.5 (2 C),
3
127.8, 127.3, 127.2, 125.5 (2 C), 122.5, 120.3, 119.7, 109.6, 105.0,
3-(1,3-Diphenyl-1H-pyrazol-5-yl)-1-ethyl-1H-indole (3n)
103.6, 44.5, 33.0, 16.0.
HRMS: m/z [M + H] calcd for C20H20N3+: 302.1652; found: 302.1659.
+
Colorless oil; yield: 80.8 mg (89%).
1
H NMR (CDCl , 600 MHz): = 7.96 (d, J = 7.0 Hz, 2 H), 7.63 (d, J = 7.8
3
Hz, 1 H), 7.47 (d, J = 7.3 Hz, 2 H), 7.42 (t, J = 7.2 Hz, 2 H), 7.33 (d, J = 7.4
Hz, 2 H), 7.31 (d, J = 7.2 Hz, 2 H), 7.26 (d, J = 7.0 Hz, 1 H), 7.25 (d, J = 7.5
Hz, 1 H), 7.13 (d, J = 7.2 Hz, 1 H), 6.93 (s, 1 H), 6.73 (s, 1 H), 4.05–4.02
3-(1-Benzyl-3-phenyl-1H-pyrazol-5-yl)-1-methyl-1H-indole (3s)
White solid; yield: 82.6 mg (91%); mp 139–140 °C.
1
H NMR (CDCl , 600 MHz): = 7.90 (d, J = 7.3 Hz, 2 H), 7.68 (d, J = 8.0
3
(m, 2 H), 1.32 (t, J = 7.1 Hz, 3 H).
Hz, 1 H), 7.40 (t, J = 7.7 Hz, 2 H), 7.32–7.25 (m, 5 H), 7.21–7.18 (m, 2
H), 7.08 (d, J = 7.4 Hz, 2 H), 6.83 (s, 1 H), 6.79 (s, 1 H), 5.43 (s, 2 H), 3.67
13
C NMR (CDCl , 150 MHz): = 152.0, 140.6, 138.6, 135.6, 133.4, 128.7
3
(2 C), 128.6 (2 C), 127.8, 127.3, 126.7, 126.6, 125.8 (2 C), 125.4 (2 C),
(s, 3 H).
122.1, 120.2, 120.1, 109.5, 105.0, 104.4, 41.0, 15.4.
13
C NMR (CDCl , 150 MHz) = 151.1, 138.8, 138.3, 136.7, 133.7, 128.6
3
HRMS: m/z [M + H] calcd for C 5H22N3+: 364.1808; found: 364.1811.
+
2
(2 C), 128.5 (2 C), 128.3, 127.8, 127.5, 127.2, 127.1, 126.4 (2 C), 125.6
2 C), 122.5, 120.3, 119.7, 109.5, 104.7, 103.7, 53.1, 32.9.
(
©
2020. Thieme. All rights reserved. Synthesis 2020, 52, A–J