Bentabed-Ababsa et al.
(CH2Cl2) as a white powder. Mp: 202 °C. 1H NMR [(CD3)2SO]: δ
7.51 (t, 1H, J ) 7.8 Hz), 7.92 (d, 1H, J ) 6.9 Hz), 8.18 (d, 1H, J
1126, 1075, 1004, 959, 832, 799, 778, 738, 694, 665, and 583 cm-1
HRMS: calcd for C22H21N3O4 (M+•) 391.1532, found 391.1578.
.
1
) 8.6 Hz). H NMR (CDCl3) δ 7.26 (dd, 1H, J ) 8.8, 7.2 Hz),
3,7-Diiodo-[1,2,3]triazolo[1,5-a]pyridine (5a). 5a was obtained
according to general procedure C (0.49 g, 66%) and isolated after
purification by flash chromatography on silica gel (heptane/AcOEt
7.60 (dd, 1H, J ) 7.1, 0.9 Hz), 7.83 (dd, 1H, J ) 8.7, 0.9 Hz). 13
C
NMR [(CD3)2SO]: δ 91.8 (C), 112.0 (C), 112.6 (C), 116.3 (CH),
129.1 (CH), 131.6 (CH), 137.0 (C). Anal. Calcd for C7H3IN4
(270.03): C, 31.14; H, 1.12; N, 20.75. Found: C, 31.20; H, 1.21;
N, 20.54.
1
50:50) as a beige powder. Mp: 144 °C. H NMR (CDCl3): δ 7.08
(dd, 1H, J ) 8.7, 6.8 Hz), 7.53 (d, 1H, J ) 5.9 Hz), 7.60 (d, 1H,
J ) 8.8 Hz). 13C NMR (CDCl3): δ 80.9 (C), 86.4 (C), 117.9 (CH),
127.1 (CH), 128.1 (CH), 136.7 (C). Anal. Calcd for C6H3I2N3
(370.92): C, 19.43; H, 0.82; N, 11.33. Found: C, 19.74; H, 0.97;
N, 11.18.
3-(6-Iodo-2-pyridyl)-[1,2,3]triazolo[1,5-a]pyridine (2′e).40 2′e
was obtained according to general procedure B (0.47 g, 73%) and
isolated after purification by flash chromatography on silica gel
1
(CH2Cl2/AcOEt 80:20) as a beige powder. Mp: 191 °C. H NMR
3-(5,6-Diiodo-2-pyridyl)-4-iodo-[1,2,3]triazolo[1,5-a]pyri-
dine (6′e). 6′e was obtained according to general procedure C (0.34
g, 30%) and isolated after purification by flash chromatography on
silica gel (CH2Cl2/AcOEt 95:5) as a white powder. Mp: 245 °C.
1H NMR [(CD3)2SO]: δ 7.03 (t, 1H, J ) 7.0 Hz), 7.76 (d, 1H, J )
8.2 Hz), 8.00 (dd, 1H, J ) 7.0, 0.65 Hz), 8.11 (d, 1H, J ) 8.2 Hz),
9.23 (dd, 1H, J ) 7.0, 0.65 Hz). 13C NMR [(CD3)2SO]: δ 82.0
(C), 101.7 (C), 118.8 (C), 117.2 (CH), 125.9 (CH), 131.9 (C), 136.3
(CH), 137.3 (CH), 139.5 (C), 147.6 (CH), 154.5 (C). Anal. Calcd
for C11H5I3N4 (573.90): C, 23.02; H, 0.88; N, 9.76. Found: C, 23.31;
H, 1.11; N, 9.86.
(CDCl3): δ 7.06 (td, 1H, J ) 6.8, 0.8 Hz), 7.37-7.44 (m, 2H),
7.60 (d, 1H, J ) 7.6 Hz), 8.27 (d, 1H, J ) 7.8 Hz), 8.59 (d, 1H,
J ) 8.9 Hz), 8.74 (d, 1H, J ) 7.0 Hz). 13C NMR (CDCl3): δ 116.2
(CH), 117.4 (C), 119.2 (CH), 121.0 (CH), 125.4 (CH), 127.1 (CH),
132.2 (C), 132.8 (CH), 135.9 (C), 138.2 (CH), 153.2 (C). Anal.
Calcd for C11H7IN4 (322.10): C, 41.02; H, 2.19; N, 17.39. Found:
C, 40.98; H, 2.32; N, 17.52.
7-Iodo-3-(2-thienyl)-[1,2,3]triazolo[1,5-a]pyridine (2f). 2f was
obtained according to general procedure B (0.25 g, 38%) and
isolated after purification by flash chromatography on silica gel
1
(CH2Cl2/AcOEt 80:20) as a beige powder. Mp: 134 °C. H NMR
7-Iodo-3-(5-iodo-2-thienyl)-[1,2,3]triazolo[1,5-a]pyridine (5f).
5f was obtained according to general procedure C (0.68 g, 75%)
and isolated after purification by flash chromatography on silica
gel (CH2Cl2) as a yellow powder. Mp: 201 °C. 1H NMR (CDCl3):
δ 7.09 (dd, 1H, J ) 9.0, 6.8 Hz), 7.22-7.32 (m, 2H), 7.53 (dd,
(CDCl3): δ 6.95 (dd, 1H, J ) 8.8, 7.0 Hz), 7.05 (dd, 1H, J ) 5.0,
3.6 Hz), 7.28 (dd, 1H, J ) 5.0, 1.0 Hz), 7.38 (dd, 1H, J ) 6.9, 0.8
Hz), 7.45 (dd, 1H, J ) 3.6, 1.0 Hz), 7.85 (dd, 1H, J ) 8.9, 0.8
Hz). 13C NMR (CDCl3): δ 86.6 (C), 118.1 (CH), 124.4 (CH), 125.5
(CH), 126.4 (CH), 127.6 (CH), 127.9 (CH), 130.4 (C), 133.3 (C),
135.5 (C). Anal. Calcd for C10H6IN3S (327.14): C, 36.71; H, 1.85;
N, 12.84; S, 9.80. Found: C, 36.46; H, 1.98; N, 12.41; S, 10.08.
([1,2,3]Triazolo[1,5-a]pyrid-7-yl) (3,4,5-Trimethoxyphenyl)
Methanol (3a). 3a was obtained according to general procedure
A′ (0.20 g, 32%) and isolated after purification by flash chroma-
tography on silica gel (AcOEt/cyclohexane 80:20) as a yellow
1
1H, J ) 6.9, 0.9 Hz), 7.92 (dd, 1H, J ) 9.0, 1.0 Hz). H NMR
[(CD3)2SO]: δ 7.25 (t, 1H, J ) 7.9 Hz), 7.36-7.41 (m, 2H), 7.75
(d, 1H, J ) 6.9 Hz), 8.21 (d, 1H, J ) 8.8 Hz). 13C NMR
[(CD3)2SO]: δ 76.1 (C), 90.0 (C), 117.7 (CH), 125.8 (CH), 127.8
(CH), 127.9 (CH), 129.5 (C), 133.4 (C), 137.9 (CH), 138.8 (C).
Anal. Calcd for C10H5I2N3S (453.04): C, 26.51; H, 1.11; N, 9.28;
S, 7.08. Found: C, 26.77; H, 1.17; N, 9.27; S, 7.27.
1
powder. Mp: <50 °C. H NMR (CDCl3): δ 3.72 (s, 9H), 6.48 (s,
7-(2-Pyridyl)-[1,2,3]triazolo[1,5-a]pyridine (4a). 4a was ob-
tained according to general procedure D (67 mg, 17%) or E (0.10
g, 26%) and isolated after purification by flash chromatography on
silica gel (CH2Cl2/AcOEt 80:20) as a white powder. Mp: 94 °C.
1H NMR (CDCl3): δ 7.39-7.45 (m, 2H), 7.82 (dd, 1H, J ) 8.7,
1.0 Hz), 7.90-7.96 (m, 2H), 8.21 (s, 1H), 8.79-8.80 (m, 1H), 9.00
(d, 1H, J ) 8.2 Hz). 13C NMR (CDCl3): δ 116.7 (CH), 118.0 (CH),
124.5 (CH), 125.3 (CH), 125.7 (CH), 126.2 (CH), 135.1 (C), 136.7
(C), 136.9 (CH), 149.2 (C), 149.9 (CH). IR (KBr) ν: 3134, 3059,
2926, 2862, 1634, 1584, 1570, 1510, 1466, 1436, 1417, 1369, 1324,
1262, 1206, 1153, 1102, 1046, 995, 976, 953, 902, 837, 769, 732,
698, 678, 627, 612, 576, and 496 cm-1. HRMS: calcd for C11H8N4
(M+•) 196.0749, found 196.0732. Anal. Calcd for C11H8N4 (196.21):
C, 67.34; H, 4.11; N, 28.55. Found: C, 67.06; H, 4.29; N, 28.29.
3-Methyl-7-(2-pyridyl)-[1,2,3]triazolo[1,5-a]pyridine (4b). 4b
was obtained according to general procedure D (0.10 g, 24%) or
E′ (0.16 g, 38%) and isolated after purification by flash chroma-
tography on silica gel (CH2Cl2/AcOEt 80:20) as a white powder.
1H), 6.74 (s, 2H), 6.83 (d, 1H, J ) 7.0 Hz), 7.17 (dd, 1H, J ) 9.0,
7.0 Hz), 7.58 (d, 1H, J ) 9.0 Hz), 7.99 (s, 1H), OH not seen. 13C
NMR (CDCl3): δ 153.6 (2C), 140.8 (C), 138.0 (C), 135.0 (C), 134.4
(C), 126.3 (CH), 126.1 (CH), 117.2 (CH), 113.3 (CH), 104.5 (2CH),
71.2 (CH), 61.2 (CH3), 56.4 (2CH3). IR (KBr) ν: 3274, 3007, 2938,
2839, 1638, 1594, 1506, 1463, 1421, 1327, 1234, 1184, 1127, 1005,
967, 815, 754, 700, 665, and 577 cm-1. HRMS: calcd for
C16H17N3O4 (M+•) 315.1219, found 315.1225.
(3-Methyl-[1,2,3]triazolo[1,5-a]pyrid-7-yl) (3,4,5-Trimethoxy-
phenyl) Methanol (3b). 3b was obtained according to general
procedure A′ (0.40 g, 61%) and isolated after purification by flash
chromatography on silica gel (AcOEt/cyclohexane 80:20) as a
1
yellow powder. Mp: 144-146 °C. H NMR (CDCl3): δ 2.62 (s,
3H), 3.82 (s, 9H), 6.48 (s, 1H), 6.72 (d, 1H, J ) 7.0 Hz), 6.80 (s,
2H), 7.17 (dd, 1H, J ) 9.0, 6.8 Hz), 7.58 (d, 1H, J ) 9.0 Hz), OH
not seen. 13C NMR (CDCl3): δ 153.8 (2C), 140.1 (C), 138.3 (C),
135.4 (C), 134.3 (C), 132.5 (C), 124.6 (CH), 117.0 (CH), 113.6
(CH), 104.5 (2CH), 71.9 (CH), 61.3 (CH3), 56.5 (2CH3), 10.8 (CH3).
IR (KBr) ν: 3468, 2943, 2831, 1639, 1595, 1509, 1450, 1422, 1332,
1224, 1176, 1129, 1076, 1002, 957, 833, 798, 771, 736, 696, 665,
582, 530, and 492 cm-1. HRMS: calcd for C17H19N3O4 (M+•)
329.1376, found 329.1357.
1
Mp: 68 °C. H NMR (CDCl3): δ 2.68 (s, 3H), 7.32 (m, 2H), 7.70
(dd, 1H, J ) 8.7, 1.0 Hz), 7.89-7.95 (m, 2H), 8.78 (d, 1H, J )
4.5 Hz), 9.02 (d, 1H, J ) 8.1 Hz). 13C NMR (CDCl3): δ 10.6 (CH3),
116.6 (CH), 117.6 (CH), 124.2 (CH), 124.4 (CH), 125.2 (CH), 133.1
(C), 134.8 (C), 136.5 (C), 136.9 (CH), 149.4 (C), 149.8 (CH). IR
(KBr) ν: 3053, 3010, 2926, 2852, 1630, 1583, 1533, 1467, 1429,
1380, 1343, 1315, 1203, 1155, 1125, 1089, 1045, 990, 947, 808,
777, 731, 696, 676, 616, and 568 cm-1. HRMS: calcd for C12H10N4
(M+•) 210.0905, found 210.0869. Anal. Calcd for C12H10N4
(210.23): C, 68.56; H, 4.79; N, 26.65. Found: C, 68.31; H, 4.78;
N, 26.53.
(3-Phenyl-[1,2,3]triazolo[1,5-a]pyrid-7-yl) (3,4,5-Trimethoxy-
phenyl) Methanol (3c). 3c was obtained according to general
procedure A′ (0.40 g, 51%) and isolated after purification by flash
chromatography on silica gel (AcOEt/cyclohexane 80:20) as a
1
yellow powder. Mp: <50 °C. H NMR (CDCl3): δ 3.74 (s, 9H),
4.95 (s, 1H), 6.48 (s, 1H), 6.75 (s, 2H), 6.79 (d, 1H, J ) 6.8 Hz),
7.20 (dd, 1H, J ) 8.9, 6.8 Hz), 7.30 (m, 1H), 7.40 (m, 2H), 7.84
(m, 3H). 13C NMR (CDCl3): δ 152.2 (2C), 139.6 (C), 137.3 (C),
135.8 (C), 133.3 (C), 130.1 (C), 129.9 (C), 128.0 (2CH), 127.1
(CH), 125.7 (2CH), 125.1 (CH), 116.2 (CH), 112.2 (CH), 103.1
(2CH), 70.0 (CH), 59.8 (CH3), 54.9 (2CH3). IR (KBr) ν: 3370,
2937, 2836, 1635, 1593, 1547, 1506, 1462, 1421, 1329, 1233, 1184,
3-Phenyl-7-(2-pyridyl)-[1,2,3]triazolo[1,5-a]pyridine (4c). 4c
was obtained according to general procedure D (0.33 g, 60%) or E
(0.36 g, 67%) and isolated after purification by flash chromatog-
raphy on silica gel (heptane/AcOEt 50:50) and recrystallization from
heptane/Et2O (30:70) as a yellow powder. Mp: 95-97 °C. 1H NMR
(CDCl3): δ 7.39-7.57 (m, 5H), 7.91-8.02 (m, 4H), 8.09 (dd, 1H,
168 J. Org. Chem. Vol. 74, No. 1, 2009