DOI: 10.1039/C8OB03171A
Organic & Biomolecular Chemistry
J= 8.68Hz, 1H), 7.61-7.54 (t, J= 7.9Hz, 2H), 7.43-7.36 (t, J=
7.8Hz, 1H), 7.07-7.02 (d, J= 8.4Hz, 2H), 3.89 (s, 3H); 13C NMR
Isolated as a colourless solid, Yield 92%, m.p 114-116°C; IR
1
(KBr): 2923, 1593, 1400, 1126, 1017, 756 cm–1; H-NMR (400
(100 MHz, CDCl3): δ 161.3, 157.8, 150.7, 138.8, 134.3 (q, J= 60 MHz, CDCl3): δ 8.34-8.32 (d, J= 8.6Hz, 2H), 8.28-8.26 (d, J=
273.63Hz), 130.8, 129.7, 129.1, 129.0, 126.9, 121.8, 116.1,
114.3, 111.7, 55.4 ppm; ESI-MS: m/z 370 [M+H]+; HRMS (ESI)
Anal. calcd. for C19H14F3N2 m/z 370.1089 [M+H]+, found
418.1077.
1-phenyl-3-(trifluoromethyl)-6-(3,4,5-trimethoxyphenyl)-1H-
pyrazolo[3,4-b]pyridine (4d).
8.3Hz, 1H), 8.02-8.00 (d, J= 8.5Hz, 2H), 7.79-7.77 (d, J= 8.4Hz,
1H), 7.66-7.64 (d, J= 8.6Hz, 2H), 7.58-7.56 (t, J= 7.45Hz, 2H),
7.42-7.39 (t, J= 7.6Hz, 1H); 13C NMR (100 MHz, CDCl3): δ
159.1, 150.0, 140.4, 138.6, 135.3(q, J= 269.2Hz), 133.6, 131.8,
65 130.3, 129.18,129.1, 127.6, 127.1,121.8,120.9,112.3 ppm; ESI-
MS: m/z 418 [M+H]+; HRMS (ESI) Anal. calcd. for
C19H12N3BrF3 m/z 418.0161 [M+H]+, found 418.0168.
4-(1-phenyl-3-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-6-
yl)benzonitrile (4i).
5
10 Isolated as a colourless solid, Yield 89%, m.p 175-177°C; IR
1
(KBr): 2937, 1591, 1497, 1336, 1127, 1016, 755 cm–1; H-NMR
(400 MHz, CDCl3): δ 8.40-8.34 (m, 2H), 8.26-8.20 (t, J= 7.9Hz,
1H), 7.80-7.70 (t, J= 8.5Hz 1H), 7.58-7.51 (m, 2H), 7.44-7.35 70 Isolated as a colourless solid, Yield 94%, m.p 200-203°C; IR
(m, 3H), 3.98 (s, 6H), 3.94 (s, 3H); 13C NMR (100 MHz, CDCl3):
15 δ 157.5, 153.5, 150.4, 140.1, 138.72 (q, J= 276.5 Hz), 133.7,
133.2, 129.8, 128.9, 126.9, 121.7, 116.4, 112.0, 104.9, 60.9, 56.2
ppm; ESI-MS: m/z 430 [M+H]+; HRMS (ESI) Anal. calcd. for
C22H19F3N3O3 m/z 430.1373 [M+H]+, found 430.1375.
6-(4-fluorophenyl)-1-phenyl-3-(trifluoromethyl)-1H-
20 pyrazolo[3,4-b]pyridine (4e).
(KBr):2923, 2923, 2222, 1491, 1398, 1133, 1014, 762 cm–1; 1H-
NMR (400 MHz, CDCl3): δ 8.37-8.29 (m, 3H), 8.26-8.23 (d, J=
8.6Hz, 2H), 7.88-7.79 (m, 3H), 7.62-7.56 (t, J= 7.9Hz, 2H), 7.45-
7.39 (t, J= 7.7Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 155.7,
75 150.3, 142.3, 138.4, 133.8 (q, J= 271.4Hz), 132.7, 130.5, 129.2,
128.1, 127.3, 121.8, 118.4, 116.8, 113.4, 112.9 ppm; ESI-MS:
m/z 365 [M+H]+; HRMS (ESI) Anal. calcd. for C19H12F3N2 m/z
365. 0956 [M+H]+, found 365.0966.
Isolated as a colourless solid, Yield 94%, m.p 128-130°C; IR
1
(KBr): 2923, 1597, 1497, 1233, 1126, 1016, 821, 755 cm–1; H-
6-(4-nitrophenyl)-1-phenyl-3-(trifluoromethyl)-1H-
NMR (400 MHz, CDCl3): δ 8.36-8.31 (d, J= 8.9Hz, 2H), 8.26- 80 pyrazolo[3,4-b]pyridine (4j).
8.22 (d, J= 8.6Hz, 1H), 8.16-8.10 (m, 2H), 7.78-7.73 (d, J=
25 8.55Hz, 1H), 7.60-7.53 (t, J= 7.9Hz, 2H), 7.42-7.36 (t, J= 7.7Hz,
1H), 7.23-7.16 (t, J= 7.5Hz, 2H); 13C NMR (100MHz, CDCl3): δ
164.0 (d, J= 250.1Hz), 157.0, 150.5, 138.7, 134.8 (q, J=
Isolated as a colourless solid, Yield 93%, m.p 167-170°C; IR
(KBr): 2922, 1593, 1491, 1348, 1130, 1015, 755 cm–1;1H-NMR
(400 MHz, CDCl3): δ 8.41-8.35 (m, 3H), 8.34-8.30 (m, 4H),
7.91-7.88 (d, J= 8.43Hz, 1H), 7.63-7.57 (t, J= 7.6Hz, 2H), 7.46-
266.29Hz), 130.0, 129.8 (d, J= 8.07Hz),129.1, 127.0, 121.8, 85 7.40 (t, J= 7.1Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 155.3,
116.3, 116.0, 115.8, 112.1 ppm; 19F NMR: -61.9, -110.95 ppm
30 ESI-MS: m/z 358 [M+H]+; HRMS (ESI) Anal. calcd. for
C19H12F4N3 m/z 358.0961[M+H]+, found 358.0975.
6-(4-chlorophenyl)-1-phenyl-3-(trifluoromethyl)-1H-
pyrazolo[3,4-b]pyridine (4f).
150.3, 148.6, 144.1, 138.4, 134.5 (q, J= 272.88Hz), 130.6, 129.2,
128.4, 127.4, 124.1, 121.9, 119.8, 117.0, 113.0 ppm; ESI-MS:
m/z 385 [M+H]+; HRMS (ESI) Anal. calcd. for C19H12F3N4O2
m/z 385.0906 [M+H]+, found 385.0918.
90 6-(benzo[d][1,3]dioxol-5-yl)-1-phenyl-3-(trifluoromethyl)-1H-
pyrazolo[3,4-b]pyridine(4k).
Isolated as a colourless solid, Yield 91%, m.p 156-158°C; IR
(KBr): 2919, 1596, 1484, 1249, 1125, 1039, 933, 806, 760 cm–1;
1H-NMR (400 MHz, CDCl3): δ 8.39-8.29 (d, J= 8.6Hz, 2H),
Isolated as a colourless solid, Yield 92%, m.p 129-131°C; IR
1
35 (KBr): 2923, 1591, 1494, 1126, 1010, 816, 752 cm–1; H-NMR
(400 MHz, CDCl3): δ 8.37-8.30 (d, J= 8.4Hz, 2H), 8.26-8.21 (d,
J= 8.3Hz, 1H), 8.07-8.03 (d, J= 8.6Hz, 2H), 7.77-7.73 (d, J=
8.4Hz, 1H), 7.59-7.53 (m, 2H), 7.49-7.43 (d, J= 8.5Hz, 2H), 7.43- 95 8.22-8.16 (d, J= 8.55Hz, 1H),7.73-7.61 (m, 3H), 7.59-7.54 (t, J=
7.36 (t, J= 7.8Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 156.7,
40 150.4, 138.6, 136.6, 136.3, 134.25 (q, J= 274.35 Hz), 130.0,
129.1, 128.8, 127.0, 122.6, 121.7, 116.3, 112.3 ppm; ESI-MS:
m/z 374 [M+H]+; HRMS (ESI) Anal. calcd. for C19H12N3Cl F3
m/z 374.0666 [M+H]+, found 374.0681.
7.5Hz, 2H), 7.42-7.34 (t, J= 7.6Hz, 1H), 6.94-6.90 (d, J= 8.3Hz,
1H), 6.04 (s, 2H) ; 13C NMR (100 MHz, CDCl3): δ 157.5, 149.4,
148.4, 138.7, 135.0 (q, J= 271.4Hz), 132.6, 129.7, 129.1, 126.9,
122.1, 121.7, 116.2, 111.9, 108.5, 107.7, 101.5 ppm; ESI-MS:
100 m/z 384 [M+H]+; HRMS (ESI) Anal. calcd. for C20H13F3N3O2
m/z 384.0954 [M+H]+, found 384.0970.
6-(4-bromophenyl)-1-phenyl-3-(trifluoromethyl)-1H-
45 pyrazolo[3,4-b]pyridine (4g).
6-(naphthalen-2-yl)-1-phenyl-3-(trifluoromethyl)-1H-
pyrazolo[3,4-b]pyridine (4l).
Isolated as a colourless solid, Yield 93%, m.p 127-129°C; IR
1
(KBr): 2924, 1589, 1488, 1398, 1126, 1011, 815, 754 cm–1; H-
Isolated as a colourless solid, Yield 90%, m.p 104-106°C; IR
NMR (500 MHz, CDCl3): δ 8.35-8.31 (d, J= 8.8Hz, 2H), 8.29- 105 (KBr): 2925, 1595, 1497, 1122, 1016 818, 752 cm–1; H-NMR
1
8.24 (d, J= 8.3Hz, 1H), 8.02-7.98 (d, J= 8.7Hz, 2H), 7.80-7.76
50 (d, J= 8.54Hz, 1H), 7.67-7.63 (d, J= 8.7Hz, 2H), 7.60-7.54 (m,
2H), 7.43-7.38 (t, J= 8.0Hz, 1H) ); 13C NMR (125 MHz, CDCl3):
δ 156.9, 150.4, 138.6, 137.2, 134.5 (q, J= 268.83 Hz), 132.1,
(400 MHz, CDCl3): δ 8.57-8.54 (m, 1H), 8.43-8.37 (d, J= 8.4Hz,
2H), 8.33-8.24 (m, 2H), 7.99-7.92 (m, 3H),7.90-7.86 (m, 1H),
7.62-7.51 (m, 4H), 7.44-7.38 (t, J= 7.6Hz, 1H); 13C NMR (100
MHz, CDCl3): δ 158.0, 150.6, 138.8, 135.6, 134.0, 133.2, 133.3
130.1, 129.1, 127.1, 124.7, 122.3, 121.8, 120.2, 116.4, 112.4 110 (q, J= 278.02Hz), 129.8, 129.1, 128.8, 128.7, 127.7, 127.5, 127.1,
ppm; ESI-MS: m/z 418 [M+H]+; HRMS (ESI) Anal. calcd. for
55 C19H12N3BrF3 m/z 418.0161 [M+H]+, found 418.0173.
6-(2-bromophenyl)-1-phenyl-3-(trifluoromethyl)-1H-
pyrazolo[3,4-b]pyridine (4h).
127.02, 126.5, 124.7, 121.8, 116.9, 112.2 ppm ; ESI-MS: m/z 390
[M+H]+; HRMS (ESI) Anal. calcd. for C24H15F3N3 m/z
390.1212 [M+H]+, found 390.1227.
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