The Journal of Organic Chemistry
Page 16 of 24
3-((4-Methyl-N-tosylphenyl)sulfonamido)-1-pivaloyl-1H-indol-5-yl pivalate (3k): 116.2 mg, 93 %,
1
2
3
1
White solid, mp 225.0 ºC (dec.), H NMR (500 MHz, CDCl3) δ 1.35 (s, 9H), 1.40 (s, 9H), 2.45 (s, 6H),
4
5
6
7
8
6.64 (d, J = 2.5 Hz, 1H), 7.02 (dd, J = 9.0, 2.5 Hz, 1H), 7.33 (d, J = 8.3 Hz, 4H), 7.48 (s, 1H), 7.88 (d, J
= 8.3 Hz, 4H), 8.46 (d, J = 9.0 Hz, 1H). 13C{1H} NMR (125 MHz, CDCl3) δ 21.7 (2C), 27.1 (3C), 28.5
(3C), 38.9, 41.3, 113.3, 115.7, 118.1, 120.0, 127.6, 128.58 (4C), 128.63, 129.7 (4C), 133.2, 136.2 (2C),
145.3 (2C), 147.7, 176.5, 176.8. IR (neat) 1750, 1708, 1377, 1358, 1311, 1167, 1119 cm–1. MS (ESI)
calcd for C32H37N2O7S2 [M+H]+ 625.2037, found 625.2037.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Methyl 3-((4-methyl-N-tosylphenyl)sulfonamido)-1-pivaloyl-1H-indole-5-carboxylate (3l): 97.4
1
mg, 84 %, White solid, mp 221.0–221.5 ºC, H NMR (500 MHz, CDCl3) δ 1.41 (s, 9H), 2.46 (s, 6H),
3.89 (s, 3H), 7.33 (d, J = 8.3 Hz, 4H), 7.54 (s, 1H), 7.63 (d, J = 1.5 Hz, 1H), 7.86 (d, J = 8.3 Hz, 4H),
8.02 (d, J = 8.9, 1.5 Hz, 1H), 8.50 (d, J = 8.9 Hz, 1H). 13C{1H} NMR (125 MHz, CDCl3) δ 21.7 (2C),
28.4 (3C), 41.4, 52.0, 116.2, 117.1, 120.7, 126.1, 126.6, 127.2, 128.6 (4C), 128.8, 129.7 (4C), 136.0
(2C), 138.1, 145.5 (2C), 166.7, 176.7. IR (neat) 1717, 1379, 1360, 1313, 1165 cm–1. MS (ESI) calcd
for C29H31N2O7S2 [M+H]+ 583.1567, found 583.1571.
N-(5-Cyano-1-pivaloyl-1H-indol-3-yl)-4-methyl-N-tosylbenzenesulfonamide (3m): 106.7 mg,
1
97 %, White solid, mp 214.0–215.0 ºC, H NMR (500 MHz, CDCl3) δ 1.42 (s, 9H), 2.49 (s, 6H), 7.17
(d, J = 1.5 Hz, 1H), 7.34 (d, J = 8.0 Hz, 4H), 7.55 (dd, J = 9.0, 1.5 Hz, 1H), 7.64 (s, 1H), 7.83 (d, J = 8.0
Hz, 4H), 8.55 (d, J = 8.5 Hz, 1H). 13C{1H} NMR (125 MHz, CDCl3) δ 21.7 (2C), 28.2 (3C), 41.5, 107.6,
115.5, 118.2, 118.8, 123.4, 126.9, 128.5 (4C), 128.7, 129.5, 129.8 (4C), 135.7 (2C), 137.2, 145.8 (2C),
176.6. IR (neat) 2221, 1715, 1363, 1348, 1308, 1169, 1086 cm–1. MS (ESI) calcd for C28H28N3O5S2
[M+H]+ 550.1465, found 550.1470.
N-(5-(1,3-Dioxoisoindolin-2-yl)-1-pivaloyl-1H-indol-3-yl)-4-methyl-N-tosylbenzenesulfonamide
1
(3n): 99.8 mg, 75 %, White solid, mp 227.5–228.0 ºC, H NMR (500 MHz, CDCl3) δ 1.39 (s, 9H),
2.44 (s, 6H), 7.23 (d, J = 2.0 Hz, 1H), 7.38 (d, J = 8.3 Hz, 4H), 7.42 (dd, J = 9.0, 2.0 Hz, 1H), 7.47 (s,
1H), 7.80 (dd, J = 5.5, 3.0 Hz, 2H), 7.92 (d, J = 8.3 Hz, 4H), 7.96 (dd, J = 5.5, 3.0 Hz, 2H), 8.61 (d, J =
ACS Paragon Plus Environment