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RSC Advances
Page 5 of 8
DOI: 10.1039/C5RA16769H
RSC Advances
ARTICLE
Yield: 90%; yellow crystals; mp 114-116 °C; IR (KBr): 3063, 2983, 346 (30), 77(15). Anal. Calcd for C27H20ClN3O2: C, 70.40; H, 5.46; N,
1722, 1596 cm-1. 1H NMR (500 MHz, CDCl3): δ = 0.82 (t, J = 7.1 Hz, 7.68. Found: C, 70.0; H, 5.02; N, 7.28.
3H, CH3), 3.96 (q, J = 7.1 Hz, 2H, OCH2), 7.37 (t, J = 7.3 Hz, 1H, Ar), Ethyl-4-(2,4-dichlorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-
7.47-7.61 (m, 8H, Ar), 7.68 (d, J = 7 Hz, 2H, Ar), 8.06 (s, 1H, b]pyridine-6-carboxylate (3f)
Pyridine), 8.23 (d, J = 7.4 Hz, 2H, Ar), 8.44 (d, J = 8.1 Hz, 2H, Ar). 13
C
Yield: 85%; yellow crystals; mp 135°C; IR (KBr): 2982, 2929, 1719,
1592 cm-1. 1H NMR (500 MHz, CDCl3): δH = 0.82 (t, J = 7.1 Hz, 3H,
CH3), 3.96 (q, J = 7.1 Hz, 2H, OCH2), 7.49-7.50 (m, 1H, Ar), 7.51-7.53
(m, 1H, Ar), 7.56-7.58 (m, 6H, Ar), 7.66-7.69 (m, 3H, Ar), 7.89 (s, 1H,
Pyridine), 8.35-8.38 (m, 2H, Ar). 13C NMR (125 MHz, CDCl3): 13.1,
62.1, 110.4, 118.8, 121.6, 126.4, 127.5, 128.3, 128.6, 128.7, 129.0,
130.2, 132.8, 133.3, 133.8, 134.9, 135.6, 136.7, 139.0, 145.4, 151.3,
155.5, 166.1. Anal. Calcd for C27H20Cl2N3O2: C, 66.40; H, 3.92; N,
8.60. Found: C, 66.0; H, 3.52; N, 8.20.
NMR (125 MHz, CDCl3): 13.1, 62.0, 110.2, 115.1, 121.6, 126.2,
127.5, 128.2, 128.4, 128.6, 128.9, 129.0, 130.0, 134.0, 135.5, 138.1,
139.3, 145.4, 151.8, 157.0, 166.6. MS: m/z (%) = 419 [M] +(100), 346
(50), 265 (30), 117 (25), 77 (15). Anal. Calcd for C27H21N3O2: C,
77.31; H, 5.05; N, 10.02; Found: C, 76.91; H, 4.65; N, 9.62.
Ethyl-4-(4-fluorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-
6-carboxylate (3b)
Yield: 85%; yellow crystals; mp 151 °C; IR (KBr): 3062, 2979, 1724,
1499 cm-1. 1H NMR (500 MHz, CDCl3): δH = 0.80 (t, J = 7.5 Hz, 3H,
CH3), 3.94 (q, J = 7.5 Hz, 2H, OCH2), 7.20-7.25 (m, 2H, Ar), 7.35-7.38
(m, 1H, Ar), 7.46-7.52 (m, 3H, Ar), 7.55-7.59 (m, 2H, Ar), 7.64-7.66
(m, 2H, Ar), 7.98 (s, 1H, Pyridine), 8.19-8.22 (m, 2H,Ar), 8.38-8.40
(m, 2H, Ar). 13C NMR (125 MHz, CDCl3): 13.1, 62.1, 110.2, 114.8,
115.9 (d, JC-F = 21.2 Hz), 121.7, 126.3, 128.3, 128.5, 128.6, 129.0,
129.5 (d, JC-F = 8.7 Hz), 133.9, 134.3, 135.7, 139.2, 145.4, 151.7,
156.0 (d, JC-F = 250 Hz), 164.1, 166.5. MS: m/z (%) = 424 [M] + (100),
418 (45), 346 (30), 77 (25). Anal. Calcd for C27H20FN3O2: C, 74.13; H,
4.61; N, 9.61; Found: C, 73.73; H, 4.21; N, 9.21.
Ethyl-1,3-diphenyl-4-p-tolyl-1H-pyrazolo[3,4-b]pyridine-6-
carboxylate (3g)
Yield: 70%; yellow crystals; mp 164 °C; IR (KBr): 2982, 2929, 1729,
1
1493, 1462 cm-1. H NMR (500 MHz, CDCl3): δH = 0.84 (t, J = 7.1 Hz,
3H, CH3), 2.48 (S, 3H, CH3), 3.98 (q, J = 7.1 Hz, 2H. OCH2), 7.39 (t, J =
8.1 Hz, 3H, Ar), 7.49-7.55 (m, 3H, Ar), 7.60 (t, J = 8.2 Hz, 2H, Ar),
7.69-7.70 (m, 2H, Ar), 8-05 (s, 1H, Pyridine), 8.15 (d, J = 8.1 Hz, 2H,
Ar), 8.47 (d, J = 7.7 Hz, 2H, Ar). 13C NMR (125 MHz, CDCl3): 13.1,
22.0, 62.3, 110.2, 115.2, 122.1, 128.7, 128.9, 129.1, 129.2, 129.3,
129.5, 129.6, 130.0, 134.0, 135.0, 138.7, 139.6, 145.4, 151.8, 157.0,
166.0. Anal. Calcd for C28H23N3O2: C, 77.58; H, 5.35; N, 9.69. Found:
C, 77.18; H, 4.95; N, 9.29.
Ethyl-4-(4-bromophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-
6-carboxylate (3c):
Yield: 80%; yellow crystals; mp 186 °C; IR (KBr): 3062, 2986, 1724,
1574 cm-1. 1H NMR (500 MHz, CDCl3): δH = 0.85 (t, J = 7.1 Hz, 3H,
CH3), 3.99 (q, J = 7.1 Hz, 2H, OCH2), 7.04 (t, J = 7,1 HZ, 1H, Ar), 7.50-
7.54 (m, 3H, Ar), 7.59.7.62 (m, 2H, Ar), 7.68-7.72 (m, 4H, Ar), 8.03 (s,
1H, Pyridine), 8.12(d, J = 8.5 Hz, 2H, Ar), 8.43 (d, J = 7.7 Hz, 2H, Ar).
13C NMR (125 MHz, CDCl3): 13.6, 62.5, 110.2, 115.2, 121.5, 126.2,
127.5, 128.2, 128.4, 128.6, 128.9, 129, 130.0, 134.0, 135.5, 138.1,
139.3, 145.5, 151.8, 157.0, 166.6. MS: m/z (%) = 497 [M+] (100), 470
(30), 242 (25), 77 (35). Anal. Calcd for C27H20BrN3O2: C, 65.07; H,
4.04; N, 8.43. Found: C, 64.67; H, 3.64; N, 8.04
Ethyl-1,3-diphenyl-4-m-tolyl-1H-pyrazolo[3,4-b]pyridine-6-
carboxylate (3h)
Yield: 70%; yellow crystals; mp 141°C; IR (KBr): 3035, 2974, 2919,
1720 cm-1. 1H NMR (500 MHz, CDCl3): δH = 0.85 (t, J = 7.1 Hz, 3H,
CH3), 2.52 (s, 3H, CH3), 3.98 (q, J = 7.1 Hz, 2H, OCH2), 7.29 (s, 1H, Ar),
7.35 (s, 1H, Ar), 7.39 (s, 1H, Ar), 7.47-7.51 (m, 1H, Ar), 7.54-7.55 (m,
2H, Ar), 7.59-7.62 (m, 2H, Ar), 7.69-7.71 (m, 2H, Ar), 8.03 (d, J = 7
Hz, 2H, Ar), 8.07 (s, 1H, Pyridine), 8.48 (d, J = 7.6 Hz, 2H, Ar). 13C
NMR (125 MHz, CDCl3) : δc = 13.17, 24.7, 60.08, 109.2, 115.2, 115.7,
121.5, 121.8, 126.1, 128.5, 128.8, 129.1, 129.8,130.7, 132.7, 134.0,
135.5,
139.3, 139.6, 145.4, 151.9, 156.8, 160.1, 166.6. Anal. Calcd for
C28H23N3O2: C, 77.58; H, 5.35; N, 9.69. Found: C, 77.18; H, 4.95; N,
9.29.
Ethyl-4-(4-methoxyphenyl)-1,3-diphenyl-1H-pyrazolo[3,4-
b]pyridine-6-carboxylate (3i)
Ethyl-4-(4-chlorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-
6-carboxylate (3d)
Yield: 80%; yellow crystals; mp 186 °C; IR (KBr): 3060, 2987, 1723,
1565 cm-1. 1H NMR (500 MHz, CDCl3): δH = 0.85 (t, J = 7.1 Hz, 3H,
CH3), 3.98 (q, J = 7.1 Hz, 2H, OCH2), 7.40 (t, J = 7Hz, 1H, Ar), 7.50-
7.56 (m, 5H, Ar), 7.59-7.62 (m, 2H, Ar), 7.68-7.70 (m, 2H, Ar), 8.03
(s, 1H, Pyridine), 8.19 (dd, J = 6.7, 1.8 Hz, 2H, Ar), 8.4 (dd, J = 8, 0.90
Hz, 2H, Ar). 13C NMR (125 MHz, CDCl3): 13.6, 62.5, 110.2, 115.2,
122.1, 128.7, 128.9, 129.1, 129.2, 129.3, 129.5, 129.6, 130.0, 134.0,
135.1, 138.7, 139.6, 145.4, 151.5, 157.4, 166.6. MS: m/z (%) = 453
[M+] (100), 418 (40), 346(35), 77(30). Anal. Calcd for C27H20ClN3O2:
C, 71.44; H, 4.44; N, 9.26. Found: C, 71.04; H, 4.04; N, 8.86.
Yield: 60%; yellow crystals; mp 169°C; IR (KBr): 3061, 2962, 2928,
1
1732, 1571 cm-1. H NMR (500 MHz, CDCl3): δH = 0.08 (t, J = 7.1 Hz,
3H, CH3), 3.91 (s, 3H, OCH3), 3.95 (q, J = 7.1 Hz, 2H, OCH2), 7.06 (d, J
= 8.8 Hz, 2H),7.25 (t, J = 7 Hz, 1H, Ar) , 7.48-7.51 (m, 3H, Ar), 7.55-
7.60 (m, 2H. Ar), 7.65-7.68 (m, 2H, Ar), 7.99 (s, 1H, Pyridine), 8.19
(d, J = 8.8 Hz, 2H, Ar), 8.43 (dd, J = 8.5, 1.1Hz, 2H, Ar), 13C NMR (125
MHz, CDCl3): 13.1, 55.4, 61.9, 109.7, 110.2, 114.3, 114.5, 121.6,
126.1, 128.2, 128.4, 128.6, 129.0, 130.7, 134.1, 135.3, 139.3, 145.4,
151.9, 156.7, 161.3, 166.7. MS: m/z (%) = 449.5 [M+] (100), 419 (40),
Ethyl-4-(2-chlorophenyl)-1,3-diphenyl-1H-pyrazolo[3,4-b]pyridine-
6-carboxylate (3e)
342 (30), 77(25). Anal. Calcd for C28H23N3O3: C, 74.82; H, 5.16; N,
9.35. Found: C, 74.42; H, 4.76; N, 8.95.
Yield: 80%; yellow crystals; mp 190°C; IR (KBr): 3062, 2975, 1731,
1595 cm-1. 1H NMR (500 MHz, CDCl3): δH = 0.83 (t, J = 7.2 Hz, 3H,
CH3), 3.97 (q, J = 7.2 Hz, 2H, OCH2), 7.34 (t, J = 7.2 Hz, 1H, Ar), 7.42-
7.45 (m, 2H, Ar), 7.51-7.56 (m, 6H, Ar), 7.68-7.75 (m, 3H, Ar), 7.92
(s, 1H, Pyridine), 8.4 (d, J = 7.8 Hz, 2H, Ar). 13C NMR (125 MHz,
CDCl3): 13.1, 62.1, 118.7, 119.1, 119.6, 121.5, 121.9, 126.3, 127.2,
128.6, 128.9, 129.2, 129.5, 130.3, 130.6, 132.1, 132.6, 133.9, 134.8,
138.3, 139.1, 156.7, 166.3. MS: m/z (%) = 435 [M+] (100), 418 (40),
Ethyl-4-(3,4-dimethoxyphenyl)-1,3-diphenyl-1pyrazolo[3,4-
b]pyridine-6-carboxylate (3j)
Yield: 65%; yellow crystals; mp 109°C; IR (KBr): 2923, 2851, 1722,
1571 cm-1. 1H NMR(500 MHz, CDCl3): δH =0.80 (t, J = 7.1 Hz, 3H,
CH3), 3.93 (q, J = 7.1 Hz, 2H, OCH2), 3.98 (s. 3H, OCH3), 4.04 (s, 3H,
OCH3), 7.02 (d, J = 8.4 Hz, 1H, Ar), 7.26-7.35 (m, 1H, Ar), 7.49-7.58
(m, 5H, Ar), 7.56-7.68 (m, 2H, Ar), 7.78-7.81 (m, 1H, Ar), 7.87 (d, J =
1.8 Hz, 1H, Ar), 8.0 (s, 1H, Pyridine), 8.44 (d, J = 7.8 Hz, 2H, Ar). 13C
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