Synthesis of novel 1,2,3-triazole-containing pyridine–pyrazole…
145.4, 139.3, 139.2, 135.8, 132.8, 128.0, 126.6, 126.6, 121.9, 121.3, 121.2, 110.1,
34.3 ppm. HRMS (ESI): m/z [M - H]? calcd. for C18H Cl79Br2N7O?, 533.9080,
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found: 533.9080; calcd. for C18H Cl79Br81BrN7O?, 535.9060, found: 535.9060;
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35-
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calcd. for C18H Cl79Br2N7O?, 535.9051, found: 535.9060; calcd. for C18H
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Cl81Br2N7O?, 537.9039, found: 537.9041; calcd. for C18H Cl79Br81BrN7O?,
537.9030, found: 537.9041; calcd. for C18H Cl81Br2N7O?, 539.9010, found:
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539.9001.
Data for 3h: Yield 49 %; yellow solid; Mp: 184.7–185.1 °C; 1H NMR
(400 MHz, DMSO-d6) d 9.66 (t, J = 5.2 Hz, 1H), 8.49 (d, J = 3.6 Hz, 1H), 8.32
(s, 1H), 8.19 (d, J = 8.0 Hz, 1H), 7.64 (dd, J = 8.0, 4.8 Hz, 1H), 7.51–7.46 (m,
3H), 7.43–7.37 (m, 2H), 4.48 (d, J = 5.6 Hz, 2H), 2.13 (s, 3H) ppm. 13C NMR
(100 MHz, DMSO-d6) d 156.7, 148.7, 147.0, 144.2, 139.4, 139.2, 136.2, 132.9,
131.3, 129.7, 128.0, 126.9, 126.6, 126.6, 125.9, 124.8, 110.3, 34.2, 17.4 ppm.
HRMS (ESI): m/z [M - H]? calcd. for C19H Cl79BrN7O?, 470.0132, found:
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470.0128; calcd. for C19H Cl81BrN7O?, 472.0111, found: 472.0110; calcd. for
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C19H Cl79BrN7O?, 472.0102, found: 472.0110; calcd. for C19H Cl81BrN7O?,
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474.0082, found: 474.0089.
Data for 3i: Yield 56 %; yellow solid; Mp: 170.2–170.5 °C; 1H NMR (400 MHz,
DMSO-d6) d 9.36 (t, J = 5.6 Hz, 1H), 8.61 (s, 1H), 8.50 (dd, J = 4.8, 1.2 Hz, 1H),
8.19 (dd, J = 8.0, 1.2 Hz, 1H), 7.72 (s, 1H), 7.68–7.61 (m, 2H), 7.46 (t, J = 8.0 Hz,
1H), 7.30–7.28 (m, 2H), 4.49 (d, J = 5.6 Hz, 2H), 2.41 (s, 3H) ppm. 13C NMR
(100 MHz, DMSO-d6) d 156.7, 148.7, 147.0, 145.07, 139.6, 139.3, 139.2, 136.6,
129.6, 129.2, 128.0, 126.6, 126.6, 121.2, 120.3, 117.0, 110.1, 34.3, 20.9 ppm.
HRMS (ESI): m/z [M - H]? calcd. for C19H Cl79BrN7O?, 470.0132, found:
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470.0131; calcd. for C19H Cl81BrN7O?, 472.0111, found: 472.0110; calcd. for
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C19H Cl79BrN7O?, 472.0102, found: 472.0110; calcd. for C19H Cl81BrN7O?,
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474.0082, found: 474.0085.
Data for 3j: Yield 25 %; yellow solid; Mp: 172.3–173.0 °C; 1H NMR (400 MHz,
DMSO-d6) d 9.37 (t, J = 5.6 Hz, 1H), 8.60 (s, 1H), 8.50 (dd, J = 4.4, 1.6 Hz, 1H),
8.19 (dd, J = 8.0, 1.6 Hz, 1H), 7.76 (d, J = 8.4 Hz, 2H), 7.64 (dd, J = 8.0, 4.8 Hz,
2H), 7.39 (d, J = 8.4 Hz, 2H), 7.29 (s, 1H), 4.48 (d, J = 5.6 Hz, 2H), 2.38 (s, 3H)
ppm. 13C NMR (100 MHz, DMSO-d6) d 157.1, 149.1, 147.5, 145.5, 139.8, 139.7,
138.7, 134.8, 130.7, 128.4, 127.1, 127.1, 121.6, 120.3, 110.6, 34.8, 21.0 ppm.
HRMS (ESI): m/z [M - H]? calcd. for C19H Cl79BrN7O?, 470.0132, found:
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470.0140; calcd. for C19H Cl81BrN7O?, 472.0111, found: 472.0108; calcd. for
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C19H Cl79BrN7O?, 472.0102, found: 472.0108; calcd. for C19H Cl81BrN7O?,
474.0082, found: 474.0076.
Data for 3k: Yield 52 %; yellow solid; Mp: 195.6–196.2 °C; 1H NMR
(400 MHz, DMSO-d6) d 9.35 (t, J = 5.2 Hz, 1H), 8.49 (d, J = 4.4 Hz, 1H), 8.25
(s, 1H), 8.19 (d, J = 8.0 Hz, 1H), 7.63 (dd, J = 8.0, 4.8 Hz, 1H), 7.59 (d,
J = 8.0 Hz, 1H), 7.52 (t, J = 8.0 Hz, 1H), 7.31 (d, J = 8.4 Hz, 1H), 7.28 (s, 1H),
7.14 (t, J = 7.6 Hz, 1H), 4.49 (d, J = 5.6 Hz, 2H), 3.84 (s, 3H) ppm. 13C NMR
(100 MHz, DMSO-d6) d 156.7, 151.5, 148.7, 147.0, 143.8, 139.4, 139.2, 130.6,
128.0, 126.6, 126.5, 125.7, 125.6, 124.9, 120.9, 113.1, 110.0, 56.1, 34.2 ppm.
HRMS (ESI): m/z [M - H]? calcd. for C19H Cl79BrN7O2?, 486.0085, found:
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486.0082; calcd. for C19H Cl81BrN7O2?, 488.0060, found: 488.0060; calcd. for
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123