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Organic & Biomolecular Chemistry
Page 6 of 9
ARTICLE
Journal Name
3-(Cyclohexylmethyl)-1,3-dimethyl-1H-pyrrolo[3,2-b]pyridin-
1,3-Dimethyl-3-propylindolin-2-one (3w):16 Yellow oilV.i1eHw ANrtMicleRO(n4l0in0e
1
2(3H)-one (3q): Yellow oil. H NMR (400 MHz, CDCl3) δ: 8.24 (d, J = MHz, CDCl3) δ: 7.28–7.24 (m, 1H), 7.17 (d, JD=O7I:.210H.1z0,319H/C),97O.B0081–072.30H4
5.2 Hz, 1H), 7.19−7.16 (m, 1H), 7.09 (d, J = 8.0 Hz, 1H), 3.25 (s, 3H), (m, 1H), 6.83 (d, J = 7.6 Hz, 1H), 3.21 (s, 3H), 1.88 (td, J1 = 24.8 Hz, J2
1.99 (dd, J1 = 14.0 Hz, J2 = 6.0 Hz, 2H), 1.92 (dd, J1 = 13.6 Hz, J2 = 6.4 = 4.4 Hz, 1H), 1.74–1.67 (m, 1H), 1.35 (s, 3H), 1.04–0.94 (m, 1H),
Hz, 2H), 1.54−1.45 (m, 3H), 1.38 (s, 3H), 1.34−1.26 (m, 1H), 1.10 (d, 0.91–0.83 (m, 1H), 0.77 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3)
J = 12.4 Hz, 1H), 0.98−0.69 (m, 6H); 13C NMR (100 MHz, CDCl3) δ: δ: 180.9, 143.3, 134.3, 127.5, 122.5, 122.4, 107.8, 48.5, 40.8, 26.0,
179.5, 155.5, 142.6, 138.0, 122.1, 113.7, 48.1, 44.1, 34.6, 33.8, 33.5, 23.7, 17.8, 14.1.
25.9, 25.8, 24.1. HRMS (ESI) [M + H]+ Calcd for C16H23N2O: 259.1805,
found: 259.1808.
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3-Butyl-1,3-dimethylindolin-2-one (3x): 16 Yellow oil. H NMR (400
MHz, CDCl3) δ: 7.26 (td, J1 = 15.2 Hz, J2 = 1.2 Hz, 1H), 7.18–7.16 (m,
3-(Cyclohexylmethyl)-1,3-dimethyl-1H-pyrrolo[2,3-b]pyridin-
1H), 7.06 (td, J1 = 14.8 Hz, J2 = 0.4 Hz, 1H), 6.84 (d, J = 8.0 Hz, 1H),
1
2(3H)-one (3r): Yellow oil. H NMR (400 MHz, CDCl3) δ: 8.18 (d, J = 3.21 (s, 3H), 1.89 (td, J1 = 25.2 Hz, J2 = 4.4 Hz, 1H), 1.76–1.72 (m, 1H),
5.2 Hz, 1H), 7.40 (d, J = 7.2 Hz, 1H), 6.98–6.95 (m, 1H), 3.31 (s, 3H), 1.35 (s, 3H), 1.22–1.15 (m, 2H), 1.01–0.92 (m, 1H), 0.91–0.80 (m,
1.99–1.94 (m, 1H), 1.75–1.70 (m, 1H), 1.54−1.48 (m, 3H), 1.34 (s, 1H), 0.77 (t, J = 7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ: 180.8,
3H), 1.30−1.21 (m, 2H), 1.01−0.76 (m, 6H); 13C NMR (100 MHz, 143.3, 134.3, 127.5, 122.43, 122.35, 107.8, 48.4, 38.3, 26.5, 26.0,
CDCl3) δ: 180.5, 156.6, 146.4, 129.8, 128.6, 117.8, 47.4, 44.9, 35.4, 23.7, 22.8, 13.7.
34.6, 34.5, 33.4, 25.9, 25.85, 25.82, 25.4, 25.2, 24.0. HRMS (ESI) [M
1
1,3-Dimethyl-3-pentylindolin-2-one (3y):16 Yellow oil. H NMR (400
MHz, CDCl3) δ: 7.26 (td, J1 = 15.2 Hz, J2 = 1.2 Hz, 1H), 7.16 (dd, J1 =
(3s):17a 7.2 Hz, J2 = 0.8 Hz, 1H), 7.06 (td, J1 = 16.0 Hz, J2 = 0.8 Hz, 1H), 6.84 (d,
+ H]+ Calcd for C16H23N2O: 259.1805, found: 259.1803.
1-Benzyl-3-(cyclohexylmethyl)-3-methylindolin-2-one
Yellow oil. 1H NMR (400 MHz, CDCl3) δ: 7.29–7.22 (m, 5H), 7.16– J = 8.0 Hz, 1H), 3.21 (s, 3H), 1.92–1.84 (m, 1H), 1.75–1.68 (m, 1H),
7.10 (m, 2H), 7.00 (t, J = 7.6 Hz, 1H), 6.73 (d, J = 7.6 Hz, 1H), 5.04 (d, 1.35 (s, 3H), 1.18–1.13 (m, 4H), 1.01–0.94 (m, 1H), 0.86–0.76 (m,
J = 15.2 Hz, 1H), 4.79 (d, J = 15.6 Hz, 1H), 2.02–1.97 (m, 1H), 1.78– 4H); 13C NMR (100 MHz, CDCl3) δ: 180.8, 143.3, 134.3, 127.5, 122.4,
1.73 (m, 1H), 1.45–1.43 (m, 4H), 1.36 (s, 3H), 1.15 (d, J = 12.8 Hz, 122.3, 107.8, 48.4, 38.4, 31.8, 26.0, 24.0, 23.7, 22.2, 13.9.
1H), 1.01–0.69 (m, 6H); 13C NMR (100 MHz, CDCl3) δ: 180.9, 142.2,
3-Hexyl-1,3-dimethylindolin-2-one (3z): Yellow oil. 1H NMR (400
136.1, 134.4, 128.6, 127.4, 127.3, 122.6, 122.2, 108.9, 47.8, 45.4,
MHz, CDCl3) δ: 7.26 (td, J1 = 15.2 Hz, J2 = 1.2 Hz, 1H), 7.16 (dd, J1 =
7.2 Hz, J2 = 0.8 Hz, 1H), 7.06 (td, J1 = 14.8 Hz, J2 = 0.8 Hz, 1H), 6.84 (d,
(3t):17a J = 8.0 Hz, 1H), 3.21 (s, 3H), 1.88 (td, J1 = 25.6 Hz, J2 = 4.8 Hz, 1H),
43.6, 34.7, 34.3, 33.9, 26.4, 26.0, 25.9.
3-(Cyclohexylmethyl)-3-methyl-1-phenylindolin-2-one
Yellow oil. 1H NMR (400 MHz, CDCl3) δ: 7.53–7.49 (m, 2H), 7.40– 1.72 (td, J1 = 25.2 Hz, J2 = 4.4 Hz, 1H), 1.34 (s, 3H), 1.21–1.11 (m, 6H),
7.38 (m, 3H), 7.23–7.15 (m, 2H), 7.10–7.06 (m, 1H), 6.84–6.82 (m, 1.01–0.92 (m, 1H), 0.80 (t, J = 6.8 Hz, 4H); 13C NMR (100 MHz, CDCl3)
1H), 2.06–2.01 (m, 1H), 1.83–1.78 (m, 1H), 1.54–1.50 (m, 4H), 1.44 δ: 180.8, 143.3, 134.3, 127.5, 122.4, 122.3, 107.8, 48.4, 38.5, 31.4,
(s, 3H), 1.30–1.27 (m, 1H), 1.01–0.82 (m, 6H); 13C NMR (100 MHz, 29.3, 26.0, 24.3, 23.7, 22.5, 13.9. HRMS (ESI) [M + H]+ Calcd for
CDCl3) δ: 180.3, 142.9, 134.7, 134.1, 129.5, 127.7, 127.3, 126.4, C16H24NO: 246.1852, found: 246.1853.
122.9, 122.7, 109.2, 47.8, 45.8, 34.9, 34.3, 33.5, 26.4, 26.1, 26.0,
25.98.
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3-Heptyl-1,3-dimethylindolin-2-one (3aa): Yellow oil. H NMR (400
MHz, CDCl3) δ: 7.27–7.23 (m, 1H), 7.16 (dd, J1 = 7.2 Hz, J2 = 0.8 Hz,
3-(Cyclohexylmethyl)-1-ethyl-3-methylindolin-2-one (3u): Yellow 1H), 7.07–7.04 (m, 1H), 6.83 (d, J = 7.6 Hz, 1H), 3.21 (s, 3H),
oil. 1H NMR (400 MHz, CDCl3) δ: 7.26–7.22 (m, 1H), 7.16 (dd, J1 = 7.2 1.92−1.85 (m, 1H), 1.75–1.68 (m, 1H), 1.34 (s, 3H), 1.22–1.14 (m,
Hz, J2 = 0.8 Hz, 1H), 7.04 (td, J1 = 14.8 Hz, J2 = 0.8 Hz, 1H), 6.85 (d, J = 8H), 1.01–0.94 (m, 1H), 0.82 (t, J = 6.8 Hz, 4H); 13C NMR (100 MHz,
7.6 Hz, 1H), 3.93–3.84 (m, 1H), 3.71–3.62 (m, 1H), 1.95–1.90 (m, CDCl3) δ: 180.8, 143.3, 134.3, 127.5, 122.4, 122.3, 107.7, 48.3, 38.5,
1H), 1.73–1.68 (m, 1H), 1.53–1.40 (m, 4H), 1.30 (s, 3H), 1.24 (t, J = 31.7, 29.6, 28.9, 26.0, 24.4, 23.7, 22.5, 13.9. HRMS (ESI) [M + H]+
7.2 Hz, 3H), 1.19–1.16 (m, 1H), 0.99–0.71 (m, 6H); 13C NMR (100 Calcd for C17H26NO: 260.2009, found: 260.2009.
MHz, CDCl3) δ: 180.5, 142.1, 134.7, 127.4, 122.8, 122.0, 108.0, 47.7,
3-Isobutyl-1,3-dimethylindolin-2-one (3ab):16 Yellow oil. 1H NMR
(400 MHz, CDCl3) δ: 7.28–7.24 (m, 1H), 7.16 (dd, J1 = 7.6 Hz, J2 = 0.8
Hz, 1H), 7.08–7.04 (m, 1H), 6.85 (d, J = 8.0 Hz, 1H), 3.22 (s, 3H),
45.4, 34.7, 34.33, 34.31, 33.60, 26.06, 26.01, 25.96, 25.91, 12.4.
HRMS (ESI) [M + H]+ Calcd for C18H26NO: 272.2009, found: 272.2010.
3-(3-(Cyclohexylmethyl)-3-methyl-2-oxoindolin-1-yl)propanenitrile 1.97–1.92 (m, 1H), 1.79–1.74 (m, 1H), 1.32 (s, 3H), 1.28–1.22 (m,
(3v): Yellow oil. 1H NMR (400 MHz, CDCl3) δ: 7.30–7.26 (m, 1H), 7.19 1H), 0.65 (d, J = 6.8 Hz, 3H), 0.61 (d, J = 10.0 Hz, 3H); 13C NMR (100
(dd, J1 = 7.2 Hz, J2 = 0.8 Hz, 1H), 7.11–7.07 (m, 1H), 6.93 (d, J = 7.6 MHz, CDCl3) δ: 181.0, 143.2, 134.2, 127.5, 122.8, 122.3, 107.9, 48.0,
Hz, 1H), 4.09–3.97 (m, 2H), 2.77–2.73 (m, 2H), 1.96–1.91 (m, 1H), 46.7, 26.14, 26.08, 25.5, 24.1, 22.8.
1.77–1.72 (m, 1H), 1.53–1.37 (m, 4H), 1.33 (s, 3H), 1.22–1.17 (m,
3-Isopentyl-1,3-dimethylindolin-2-one (3ac): Yellow oil. 1H NMR
(400 MHz, CDCl3) δ: 7.26 (td, J1 = 15.2 Hz, J2 = 1.2 Hz, 1H), 7.16 (dd,
J1 = 7.2 Hz, J2 = 0.8 Hz, 1H), 7.06 (td, J1 = 14.8 Hz, J2 = 0.8 Hz, 1H),
6.84 (d, J = 7.6 Hz, 1H), 3.21 (s, 3H), 1.89 (td, J1 = 25.6 Hz, J2 = 4.4 Hz,
1H), 1.73 (td, J1 = 25.6 Hz, J2 = 4.0 Hz, 1H), 1.44–1.38 (m, 1H), 1.35 (s,
3H), 0.92–0.84 (m, 1H), 0.77 (t, J = 6.8 Hz, 6H), 0.73–0.65 (m, 1H);
1H), 1.01–0.75 (m, 6H); 13C NMR (100 MHz, CDCl3) δ: 181.1, 141.0,
134.2, 127.7, 123.2, 122.9, 117.0, 107.8, 47.7, 45.2, 35.8, 34.7, 34.3,
33.6, 26.2, 25.94, 25.92, 25.86, 16.1. HRMS (ESI) [M + H]+ Calcd for
C19H25N2O: 297.1961, found: 297.1970.
6 | Org. Biomol.Chem.
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