Molecules 2018, 23, 2265
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2.90–2.85 (m, 2H), 2.19 (s, 3H), 1.91–1.82 (m, 2H), 1.68–1.61 (m, 2H). 13C-NMR (126 MHz, DMSO-d6)
δ
179.0, 141.3, 132.2, 129.9, 129.0, 128.81, 128.78, 128.6, 121.3, 118.5, 50.1, 46.5, 44.8, 26.8, 22.0, 16.5. IR
+
ν
(KBr, film, cm−1): 3392, 2946, 2838, 1702, 1458, 694. HRMS (ESI): calcd for C19H23ON2 [M + H]+:
max
295.1805, found: 295.1804.
1
3-(3-((4-Methylbenzyl)amino)propyl)indolin-2-one (1g): Yellow oil. H-NMR (300 MHz, CDCl3)
δ
8.04
(br, 1H), 7.22–7.10 (m, 6H), 7.03–6.98 (t, J = 7.2 Hz, 1H), 6.85–6.83 (m, 1H), 3.71 (s, 2H), 3.49–3.46
(t, J = 6.0 Hz, 1H), 2.65–2.60 (t, J = 7.2 Hz, 2H), 2.32 (s, 3H), 2.02–1.97 (m, 2H), 1.72 (br, 1H), 1.64–1.52
(m, 2H). 13C-NMR (126 MHz, CDCl3)
109.6, 53.5, 48.9, 45.7, 28.1, 26.0, 21.1. IR
751. HRMS (ESI): calcd for C19H23ON2+ [M + H]+: 295.1805, found: 295.1804.
δ 180.2, 141.6, 136.9, 136.5, 129.5, 129.1, 128.1, 127.8, 124.1, 122.2,
ν
(KBr, film, cm−1): 3204, 3022, 2923, 2857, 1706, 1620, 1486,
max
1
3-(3-((4-Methoxybenzyl)amino)propyl)indolin-2-one (1h): Yellow oil. H-NMR (300 MHz, DMSO-d6)
δ
10.34 (br, 1H), 7.23–7.13 (m, 4H), 6.96–6.91 (t, J = 7.5 Hz, 1H), 6.85–6.81 (m, 3H), 3.71 (s, 3H), 3.56 (s, 2H),
3.42–3.38 (t, J = 5.7 Hz, 1H), 2.97 (br, 1H), 2.46–2.41(t, J = 7.2 Hz, 2H), 1.89–1.79 (m, 2H), 1.43–1.37
(m, 2H). 13C-NMR (126 MHz, DMSO-d6)
δ 178.9, 158.0, 142.8, 132.6, 129.7, 129.1, 127.5, 123.9, 121.2,
113.4, 109.1, 54.9, 52.2, 48.3, 45.0, 27.7, 25.5. IR ν
max (KBr, film, cm−1): 3197, 2933, 2835, 1698, 1471, 1177,
751. HRMS (ESI): calcd for C19H23O2N2+ [M + H]+: 311.1765, found: 311.1747.
3-(3-((4-Fluorobenzyl)amino)propyl)indolin-2-one (1i): Yellow solid, m.p. 101–103 ◦C 1H-NMR (300 MHz,
DMSO-d6)
1H), 6.84–6.82 (d, J = 7.8 Hz, 1H), 4.05 (s, 2H), 3.50–3.48 (t, J = 5.7 Hz, 1H), 2.87–2.82 (t, J = 7.8 Hz, 2H),
1.89–1.82 (m, 2H), 1.67–1.59 (m, 2H). 13C-NMR (101 MHz, DMSO-d6)
178.5, 163.4, 161.0, 142.7, 132.3,
132.3, 129.2, 128.6, 127.6, 124.0, 121.2, 115.4, 115.2, 109.2, 49.1, 46.2, 44.5, 26.9, 22.0. 19F NMR (377 MHz,
DMSO-d6) δ −113.9(s). IR
(KBr, film, cm−1): 3361, 2920, 2849, 1703, 1471, 1226, 751. HRMS (ESI):
δ 10.42 (s, 1H), 8.86 (br, 1H), 7.57–7.52 (m, 2H), 7.28–7.15 (m, 4H), 6.98–6.93 (t, J = 7.5 Hz,
δ
ν
max
calcd for C18H20ON2F+ [M + H]+: 299.1554, found: 299.1553.
1
3-(3-((4-Chlorobenzyl)amino)propyl)indolin-2-one (1j): Yellow oil. H-NMR (300 MHz, CDCl3)
δ
8.76 (br,
1H), 7.31–7.28 (m, 1H), 7.25–7.17(m, 5H), 7.03–6.98 (t, J = 7.5 Hz, 1H), 6.87–6.84 (d, J = 7.8 Hz, 1H),
3.72 (s, 2H), 3.49–3.45 (t, J = 5.7 Hz, 1H), 2.64–2.59 (t, J = 7.2 Hz, 2H), 2.24–2.19 (m, 1H), 2.04–1.97 (dd,
J = 14.1, 7.8 Hz, 2H), 1.62–1.51 (m, 2H). 13C-NMR (126 MHz, CDCl3) δ 180.2, 141.6, 138.3, 132.7, 129.5,
129.4, 128.5, 127.9, 124.1, 122.3, 109.7, 53.0, 48.7, 45.7, 28.0, 25.9. IR
ν
max (KBr, film, cm−1): 3200, 2932,
1714, 1471, 1015, 751. HRMS (ESI): calcd for C18H20ON2Cl+ [M + H]+: 315.1259, found: 315.1256.
◦
1
3-(3-((4-Bromobenzyl)amino)propyl)indolin-2-one (1k): Yellow solid, m.p. 102–104 C. H-NMR (300
MHz, DMSO-d6) 10.41 (s, 1H), 8.33 (br, 1H), 7.60–7.58 (d, J = 8.1 Hz, 2H), 7.44–7.41 (d, J = 8.1 Hz,
δ
2H), 7.27–7.24 (d, J = 7.2 Hz, 1H), 7.20–7.15 (t, J = 7.8 Hz, 1H), 6.97–6.92 (t, J = 7.5 Hz, 1H), 6.84–6.81
(d, J = 7.8 Hz, 1H), 3.96 (s, 2H), 3.48–3.44 (t, J = 5.7 Hz, 1H), 2.80–2.74 (t, J = 7.5 Hz, 2H), 1.91–1.80
(m, 2H), 1.64–1.55 (m, 2H). 13C-NMR (75 MHz, DMSO-d6)
δ 178.6, 142.7, 131.8, 131.3, 129.3, 127.7, 124.0,
121.6, 121.2, 109.2, 49.8, 46.8, 44.7, 26.9, 22.7. IR
ν
(KBr, film, cm−1): 3366, 3197, 2922, 2850, 1702,
max
1622, 1471, 753. HRMS (ESI): calcd for C18H20ON2Br+ [M + H]+: 359.0754, found: 359.0740.
1
6-Fluoro-3-(3-((4-(trifluoromethyl)benzyl)amino)propyl)indolin-2-one (1l): Orange oil. H-NMR (300 MHz,
DMSO-d6)
6.81–6.67 (m, 2H), 3.77 (s, 2H), 3.48–3.44 (t, J = 6.3Hz, 1H), 2.56 (s, 1H), 1.95–1.87 (m, 3H), 1.49–1.41
(m, 3H). 13C-NMR (126 MHz, DMSO-d6)
179.8, 163.3, 161.4, 146.5, 144.8, 144.7, 128.9, 125.9, 125.6,
125.5, 125.30, 125.27, 107.7, 107.5, 97.9, 97.7, 52.8, 49.0, 45.0, 28.1, 26.0. 19F NMR (377 MHz, DMSO-d6)
δ −60.86(s), 113.93 (s). IR
max (KBr, film, cm−1): 3633, 2952, 2855, 1717, 1558, 1329, 1020, 849, 737.
HRMS (ESI): calcd for C19H19ON2F4+ [M + H]+: 367.1428, found: 367.1422.
δ 10.56 (br, 1H), 7.69–7.66 (d, J = 7.8 Hz, 2H), 7.58–7.55 (d, J = 7.8 Hz, 2H), 7.30–7.25 (m, 1H),
δ
−
ν
1
6-Chloro-3-(3-((4-(trifluoromethyl)benzyl)amino)propyl)indolin-2-one (1m): Orange oil. H-NMR (300 MHz,
DMSO-d6) 10.57 (br, 1H), 7.71–7.68 (d, J = 7.8 Hz, 2H), 7.58–7.56 (d, J = 7.8 Hz, 2H), 7.30–7.28 (m, 1H),
7.05–7.02 (m, 1H), 6.89 (s, 1H), 3.77 (s, 2H), 3.52–3.48 (t, J = 5.7 Hz, 1H), 2.57 (s, 1H), 1.97–1.86 (m, 3H),
1.50–1.38 (m, 3H). 13C-NMR (126 MHz, DMSO-d6)
178.9, 146.1, 144.3, 131.8, 128.6, 128.4, 125.3, 124.83,
δ
δ