Molecules 2021, 26, 2402
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1:3). IR (KBr): 3419, 3056, 3027, 2971, 2930, 1752, 1705, 1634, 1594, 1519, 1497, 1467, 1435,
1281, 1255, 1190, 1167, 1112, 1101, 1015, 964, 916, 875, 804, 777, 730, 711, 696, 600 cm−1
.
1H-NMR (600 MHz, CDCl3),
δ = 7.83 (d, J = 8.5 Hz, 2H), 7.32–7.28 (m, 3H), 7.27–7.21 (m,
2H), 7.17 (ddd, J = 8.0, 7.1, 1.0 Hz, 1H), 7.14–7.09 (m, 4H), 7.08–7.04 (m, 3H), 6.93 (s, 1H),
6.71 (d, J = 5.5 Hz, 2H), 5.33 (s, 1H), 5.30 (d, J = 16.2 Hz, 1H), 5.26 (d, J = 16.2 Hz, 1H),
4.17 (q, J = 7.2 Hz, 2H), 4.14–4.00 (m, 2H), 3.86 (s, 3H), 2.34 (s, 3H), 1.24 (t, J = 7.2 Hz, 3H).
13C-NMR (150 MHz, CDCl3),
δ = 170.8, 167.4, 153.1, 152.0, 137.5, 137.2, 137.0, 131.7, 130.6
(2C), 129.6 (2C), 128.9 (2C), 128.5 (2C), 127.8 (2C), 127.2, 126.6(2C), 124.0, 122.6, 122.3, 122.2,
119.9, 119.4, 113.9, 110.2, 61.3, 51.9, 50.3, 44.2, 43.5, 21.3, 14.3. MS (ESI): m/z = 574 [M + H]+;
HRMS (TOF ES+): m/z [M + H]+ calcd for C36H36N3O4+: 574.2700; found: 574.2703.
Ethyl-2-(2-(1-benzyl-1H-indol-3-yl)-N’-(tert-butyl)-2-(4-methoxyphenyl)acetimidamido)acetate
(10d) Brownish oil; yield 100 mg (43%, method A); Rf = 0.40 (EtOAc– hexane, 1:1). IR (KBr):
3412, 3059, 3030, 2957, 2932, 2836, 1738, 1638, 1611, 1583, 1510, 1466, 1453, 1357, 1249, 1177,
1
1110, 1034, 820, 808, 742, 696 cm−1. H-NMR (600 MHz, CDCl3),
δ = 7.51 (d, J = 8.0 Hz, 1H),
7.29–7.21 (m, 6H), 7.20–7.06 (m, 2H), 7.02–6.96 (m, 2H), 6.87 (d, J = 8.8 Hz, 2H), 6.64 (s, 1H),
5.35 (s, 1H), 5.29 (d, J = 16.2 Hz, 1H), 5.23 (d, J = 16.2 Hz, 1H), 4.24–4.00 (m, 5H), 3.81 (s,
3H), 1.26 (s, 12H). 13C-NMR (150 MHz, CDCl3),
δ = 173.2, 158.9, 158.6, 137.7, 137.1, 131.8,
129.8 (2C), 128.9 (2C), 128.5, 127.7, 127.5, 126.4 (2C), 122.5, 119.9, 119.8, 115.4, 114.3 (2C),
110.0, 60.4, 57.8, 55.4, 51.1, 50.1, 43.4, 28.6 (3C), 14.4. MS (ESI): m/z = 512 [M + H]+; HRMS
(TOF ES+): m/z [M + H]+ calcd for C32H38N3O3+: 512.2908; found: 512.2911.
Ethyl-2-((2-(1-benzyl-1H-indol-3-yl)-1-((benzyloxy)amino)-2-(4-methoxyphenyl)ethylidene)
amino)acetate (10e). Orange oil; yield 205 mg (73%, method A); Rf = 0.67 (EtOAc-hexane, 1:3).
IR (KBr): 3403, 3059, 3030, 2979, 2931, 2836, 1743, 1632, 1611, 1510, 1496, 1466, 1453, 1370,
1
1247, 1201, 1177, 1028, 820, 741, 697cm−1. H-NMR (600 MHz, CDCl3, mixture of tautomers
1:1), δ = 7.42 (d, J = 8.0 Hz, 1H), 7.39–7.36 (m, 2H), 7.33–7.26 (m, 12H), 7.26–7.19 (m, 9H),
7.17–7.12 (m, 2H), 7.09–7.05 (m, 4H), 7.04–7.00 (m, 2H), 6.87 (dd, J = 8.6 Hz, 2H), 6.84–6.80
(m, 4H), 6.02 (s, 1H), 5.72 (br s, 1H), 5.29–5.22 (m, 4H), 5.17 (s, 1H), 5.02–4.97 (m, 2H),
4.92–4.83 (m, 2H), 4.22 (br s, 1H), 4.16–4.02 (m, 4H), 3.90–3.75 (m, 4H), 3.81 (s, 3H), 3.79 (s,
3H), 1.20 (t, J = 7.2 Hz, 3H), 1.18 (t, J = 7.2 Hz, 3H). 13C-NMR (150 MHz, CDCl3, mixture of
tautomers 1:1),
δ = 170.8, 170.5, 158.5, 158.4, 158.1, 154.5, 138.9, 138.8, 137.8, 137.6, 137.0,
136.9, 131.9, 131.4, 129.9 (2C), 129.8 (2C), 128.9 (2C), 128.8 (2C), 128.7, 128.5 (2C), 128.4 (2C),
128.3 (2C), 128.1 (2C), 128.0, 127.7, 127.6, 127.59, 127.57, 127.4, 126.6 (2C), 122.3, 122.1, 120.0,
119.7, 119.6, 119.5, 114.3, 114.03 (2C), 113.98, 113.8 (2C), 110.0, 109.9, 75.6, 75.3, 61.4, 61.0,
55.4, 55.3, 50.2, 50.1, 44.7, 43.9, 42.8, 40.2, 14.24, 14.18. MS (ESI): m/z = 562 [M
−
H]+; HRMS
(TOF ES+): m/z [M − H]+ calcd for C35H36N3O4+: 562.2711; found: 562.2706.
Ethyl-2-(2-(1-benzyl-1H-indol-3-yl)-N’-(benzyloxy)-2-(p-tolyl)acetimidamido)acetate (10f).
Orange oil; yield 109 mg (60%, method A); Rf = 0.44 (EtOAc-hexane, 1:5). IR (KBr): 3405,
3028, 2979, 2919, 2861, 1742, 1631, 1511, 1496, 1467, 1453, 1371, 1334, 1200, 1024, 910,
1
807, 777, 740, 697 cm−1. H-NMR (600 MHz, CDCl3, mixture of tautomers 1:1),
δ = 7.42
(d, J = 8.0 Hz, 1H), 7.40–7.37 (m, 2H), 7.33–7.26 (m, 11H), 7.26–7.18 (m, 10H), 7.17–7.12 (m,
4H), 7.09 (d, J = 8.0 Hz, 2H), 7.08–7.05 (m, 4H), 7.02 (ddd, J = 8.0, 7.0, 1.0 Hz, 2H), 6.83 (dd,
J = 2.9, 0.7 Hz, 2H), 6.04 (s, 1H), 5.73 (br s, 1H), 5.29–5.23 (m, 4H), 5.20 (s, 1H), 5.00 (m, 2H),
4.91–482 (m, 2H), 4.23 (br s, 1H), 4.11–4.00 (m, 4H), 3.91–3.75 (m, 4H), 2.36 (s, 3H), 2.33 (s,
3H), 1.20 (t, J = 7.2 Hz, 3H), 1.18 (t, J = 7.2 Hz, 3H). 13C-NMR (150 MHz, CDCl3, mixture of
tautomers 1:1),
δ = 170.8, 170.5, 158.1, 154.4, 138.9, 138.8, 137.8, 137.6, 137.0, 136.9, 136.7,
136.4, 136.3, 136.2, 129.4 (2C), 129.2 (2C), 128.9 (2C), 128.8 (2C), 128.7 (2C), 128.6, 128.5 (2C),
128.3 (2C), 128.1 (2C), 128.0, 127.8, 127.7. 127.6, 127.5 (2C), 127.4, 127.1, 126.8, 126.6 (2C),
126.5 (2C), 122.3, 122.1, 120.0, 119.7, 119.6, 119.5, 114.1, 113.8, 110.0, 109.8, 75.6, 75.3, 61.3,
61.0, 50.2, 50.1, 44.7, 43.9, 43.2, 40.6, 21.3, 21.2, 14.3, 14.2. MS (ESI): m/z = 546 [M
−
H]+;
HRMS (TOF ES+): m/z [M − H]+ calcd for C35H36N3O3+: 546.2762; found: 546.2756.
4. Conclusions
We have developed a new three-component reaction of 3-arylidene-3H-indolium
salt, isocyanide and amine leading to N,N-disubstituted aryl(indol-3-yl)acetimidamides