B. L. Kuhn et al. / Tetrahedron Letters xxx (2014) xxx–xxx
1595, 1498, 1322, 1038, 766 and 740 cmÀ1
5
(d, 1H, J = 8.1 Hz), 7.47 (d, 1H, J = 7.7 Hz), 7.27–7.23 (m, 1H), 7.16–7.12 (m, 1H),
4.22 (t, 2H, J = 6.8 Hz), 1.85–1.75 (m, 2H), 1.28–1.22 (m, 10H) and 0.85–0.83
(m, 3H). 13C NMR d: 155.1, 136.4, 135.5, 128.6, 122.1, 120.3, 118.1, 110.6, 93.0,
45.8, 30.9, 29.3, 28.3, 25.9, 21.7 and 13.6. EI-MS (m/z, rel int.,%): 331 [(M+2)+,
2], 330 [(M+1)+, 7], 329 (M+, 33), 272 (57), 260 (59), 162 (100), 130 (28), 77 (8),
57 (26) and 41 (50). Anal. Calcd: C, 61.97; H, 7.04. Found: C, 61.74; H, 7.23.
3-((1H-Tetrazol-5-yl)thio)-1-phenyl-1H-indole (5g). Yellow solid, mp:
.
1H NMR d: 7.45–7.34 (m, 6H), 6.82
(dd, J = 3.6 Hz, 1.6 Hz, 1H) and 6.40–6.38 (m, 1H). 13C NMR d: 155.0, 138.3,
128.7, 128.1, 127.7, 126.0, 121.6, 111.4 and 109.9. EI-MS (m/z, rel int.,%): 244
[(M+1)+, 2], 243 (M+, 6), 242 (37), 185 (34), 174 (45), 173 (100), 172 (48), 130
(16), 115 (19), 77 (65), 70 (26) and 51 (39). HRMS obsd m/z: 266.0465;
C
11H9N5SNa [M+Na]+ requires m/z 266.0476. 5-((1-(4-Methoxyphenyl)-1H-
pyrrol-2-yl)thio)-1H-tetrazole (6b). White solid, mp: 210.0–211.4 °C. IR (KBr,
153.1–154.3 °C. IR (KBr,
m
): 3033, 2331, 1598, 1499, 1457, 1231, 1017, 746
m
): 3012, 2360, 1517, 1250, 1039, 837 and 740 cmÀ1 1H NMR d: 7.27–7.24 (m,
.
and 695 cmÀ1
.
1H NMR dd: 8.22 (d, J = 0.9 Hz, 1H), 7.66–7.56 (m, 6H), 7.49–7.45
3H), 6.96 (d, J = 8.9 Hz, 2H), 6.78 (dd, J = 3.6 Hz, 1.7 Hz, 1H), 6.39–6.35 (m, 1H)
and 3.76 (s, 3H). 13C NMR d: 158.6, 155.1, 131.3, 128.4, 127.5, 121.2, 113.9,
111.5, 109.6 and 55.2. EI-MS (m/z, rel int.,%): 275 [(M+2)+, 2], 274 [(M+1)+, 6],
273 (M+, 37), 216 (20), 204 (100), 173 (37), 92 (15) and 77 (20). Anal. Calcd: C,
52.73; H, 4.06. Found: C, 52.86; H, 4.31. 5-((1-(4-Chlorophenyl)-1H-pyrrol-2-
(m, 1H), 7.33–7.29 (m, 1H) and 7.26–7.22 (m, 1H). 13C NMR d: 154.9, 137.9,
136.0, 135.5, 129.8, 129.1, 127.3, 124.2, 123.5, 121.6, 118.6, 111.1 and 96.9. EI-
MS (m/z, rel int.,%): 294 [(M+1)+, 5], 293 (M+, 29), 236 (36), 224 (100), 121 (21)
and 77 (40). HRMS obsd m/z: 316.0614; C15H11N5SNa [M+Na]+ requires m/z
316.0633. 3-((1H-Tetrazol-5-yl)thio)-5-bromo-1-methyl-1H-indole (5h). Beige
yl)thio)-1H-tetrazole (6c). Orange solid, mp: 171.2–173.1 °C. IR (KBr,
m): 3129,
solid, mp: 205.5–207.0 °C. IR (KBr,
m
): 3394, 1509, 1465, 1242, 795 and
3010, 2362, 1494, 1311, 1094, 837 and 739 cmÀ1 1H NMR d: 7.50 (d, J = 8.8 Hz,
.
614 cmÀ1
.
1H NMR d: 7.87 (s, 1H), 7.62 (d, J = 1.7 Hz, 1H), 7.52 (d, J = 8.7 Hz,
2H), 7.40 (d, J = 8.8, 2H), 7.35 (dd, 1H, J = 3.0 Hz, 1.8 Hz), 6.82 (dd, J = 3.7, 1.8,
1H) and 6.40 (dd, 1H, J = 3.7 Hz, 3.0 Hz). 13C NMR d: 155.0, 137.2, 132.4, 128.8
128.3, 127.9, 122.0, 111.6 and 110.2. EI-MS (m/z, rel int.,%): 279 [(M+2)+, 6],
278 [(M+1)+, 2], 277 (M+, 18), 219 (19), 173 (100), 111 (13) and 75 (19). HRMS
obsd m/z: 300.0074; C11H8ClN5SNa [M+Na]+ requires m/z 300.0087.
1H), 7.36 (dd, J = 8.7 Hz, 1.8 Hz, 1H) and 3.82 (s, 3H). 13C NMR d: 155.2, 137.6,
135.8, 130.6, 124.7, 120.5, 113.2, 112.8, 94.3 and 33.0. EI-MS (m/z, rel int.,%):
310 [(M+2)+, 35], 309 [(M+1)+, 5], 308 (M+, 35), 253 (48), 241 (97), 239 (100),
162 (24), 117 (32) and 77 (7). HRMS obsd m/z: 331.9575; C10H8BrN5SNa
[M+Na]+ requires m/z 331.9581. 5-((1-Phenyl-1H-pyrrol-2-yl)thio)-1H-
tetrazole (6a). Yellow solid, mp: 160.1–161.4 °C. IR (KBr,
m): 3048, 2366,