WU ET AL.
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to 1.44 (m, 2 H), 0.97 (t, J = 7.4 Hz, 3 H). 13C NMR (151
MHz, CDCl3) δ 146.93, 142.93, 139.85, 135.39, 131.05,
128.58, 121.78, 121.12, 119.71, 112.40, 109.51, 74.15,
70.85, 31.98, 31.79, 19.44, 14.00.
3,3′‐bis((isopentyloxy)methyl)‐9,9′‐dimethyl‐9H,9′
H‐1,1′‐bipyrido[3,4‐b]indole (4h) (yield of 85%) MS‐
ESI, m/z 585.32 [M + Na]+. HR‐MS‐EI m/z calcd for
C36H42N4O2 [M + H]+ 563.3378, found: 563.3386. 1H
NMR (600 MHz, CDCl3) δ 8.20 (s, 1 H), 8.16 (d, J = 7.9
Hz, 1 H), 7.51 (t, J = 8.2 Hz, 1 H), 7.28 (d, J = 8.3 Hz, 1
H), 7.23 (t, J = 7.5 Hz, 1 H), 4.81 (d, J = 3.1 Hz, 2 H),
3.61 (t, J = 6.8 Hz, 2 H), 3.16 (s, 3 H), 1.74 (td, J = 13.4,
6.7 Hz, 1 H), 1.55 (q, J = 6.8 Hz, 2 H), 0.88 (d, J = 6.7
Hz, 6 H). 13C NMR (151 MHz, CDCl3) δ 145.89, 141.90,
138.80, 134.36, 130.03, 127.57, 120.75, 120.08, 118.69,
111.39, 108.48, 73.16, 68.50, 37.70, 30.76, 24.20, 21.72.
3,3′‐bis((pentan‐3‐yloxy)methyl)‐9,9′‐dimethyl‐
3,3′‐bis((pentyloxy)methyl)‐9,9′‐dimethyl‐9H,9′H‐
1,1′‐bipyrido[3,4‐b]indole (4d) (yield of 94%) MS‐ESI,
m/z 585.32 [M + Na]+. HR‐MS‐EI m/z calcd for
C36H42N4O2 [M + H]+ 563.3359, found: 563.3386. 1H
NMR (600 MHz, CDCl3) δ 8.28 (s, 1 H), 8.24 (d, J = 7.8
Hz, 1 H), 7.59 (t, J = 7.7 Hz, 1 H), 7.36 (d, J = 8.3 Hz, 1
H), 7.31 (t, J = 7.5 Hz, 1 H), 4.89 (d, J = 3.4 Hz, 2 H),
3.66 (t, J = 6.7 Hz, 2 H), 3.24 (s, 3 H), 1.76 to 1.71 (m, 2
H), 1.45 to 1.40 (m, 2 H), 1.38 (dd, J = 14.2, 6.5 Hz, 2
H), 0.93 (t, J = 7.2 Hz, 3 H). 13C NMR (151 MHz, CDCl3)
δ 146.92, 142.93, 139.85, 135.39, 131.05, 128.58, 121.77,
121.12, 119.71, 112.41, 109.50, 74.15, 71.16, 31.80, 29.57,
28.45, 22.60, 14.08.
3,3′‐bis((hexyloxy)methyl)‐9,9′‐dimethyl‐9H,9′H‐
1,1′‐bipyrido[3,4‐b]indole (4e) (yield of 94%) MS‐ESI,
m/z 613.35 [M + Na]+. HR‐MS‐EI m/z calcd for
C38H46N4O2 [M + H]+ 591.3672, found: 591.3699. 1H
NMR (600 MHz, CDCl3) δ 8.27 (s, 1 H), 8.23 (d, J = 7.8
Hz, 1 H), 7.59 (t, J = 7.2 Hz, 1 H), 7.36 (d, J = 8.3 Hz, 1
H), 7.31 (t, J = 7.5 Hz, 1 H), 4.89 (d, J = 3.6 Hz, 2 H),
3.66 (t, J = 6.7 Hz, 2 H), 3.24 (s, 3 H), 1.73 (dd, J =
14.6, 7.4 Hz, 2 H), 1.44 (dd, J = 14.9, 7.2 Hz, 2 H), 1.36
to 1.32 (m, 4 H), 0.90 (t, J = 6.9 Hz, 3 H). 13C NMR
(151 MHz, CDCl3) δ 146.92, 142.93, 139.85, 135.39,
131.05, 128.58, 121.77, 121.12, 119.71, 112.41, 109.50,
74.15, 71.18, 31.80, 31.76, 29.85, 25.95, 22.67, 14.06.
3,3′‐bis (isopropoxymethyl)‐9,9′‐dimethyl‐9H,9′H‐
1,1′‐bipyrido[3,4‐b]indole (4f) (yield of 87%) MS‐ESI,
m/z 529.25 [M + Na]+. HR‐MS‐EI m/z calcd for
C32H34N4O2 [M + H]+ 507.2744, found: 507.2760. 1H
NMR (600 MHz, CDCl3) δ 8.30 (s, 1 H), 8.24 (d, J = 7.9
Hz, 1 H), 7.58 (t, J = 7.7 Hz, 1 H), 7.35 (d, J = 8.3 Hz, 1
H), 7.30 (t, J = 7.5 Hz, 1 H), 4.91 (s, 2 H), 3.88 (dq, J =
12.2, 6.1 Hz, 1 H), 3.23 (s, 3 H), 1.33 (d, J = 4.0 Hz, 6
H). 13C NMR (151 MHz, CDCl3) δ 147.43, 142.92,
139.78, 135.32, 131.07, 128.54, 121.82, 121.15, 119.66,
112.18, 109.48, 71.78, 71.49, 31.78, 22.32.
9H,9′H‐1,1′‐bipyrido[3,4‐b]indole (4i) (yield of 74%)
MS‐ESI, m/z 585.32 [M + Na]+. HR‐MS‐EI m/z calcd
1
for C36H42N4O2 [M + H]+ 563.3373, found: 563.3386. H
NMR (600 MHz, CDCl3) δ 8.26 (s, 1 H), 8.17 (d, J = 7.8
Hz, 1 H), 7.52 (t, J = 7.7 Hz, 1 H), 7.29 (d, J = 8.3 Hz, 1
H), 7.24 (t, J = 7.5 Hz, 1 H), 4.84 (s, 2 H), 3.38 (dd, J =
11.6, 5.8 Hz, 1 H), 3.16 (s, 3 H), 1.60 (dd, J = 13.3, 6.8
Hz, 4 H), 0.96 to 0.91 (m, 6 H). 13C NMR (151 MHz,
CDCl3) δ 147.71, 142.93, 139.66, 135.33, 131.08, 128.54,
121.82, 121.18, 119.65, 112.28, 109.48, 82.21, 71.99,
31.77, 26.02, 9.75.
3,3′‐bis(((2,4‐dimethylpentan‐3‐yl)oxy)methyl)‐
9,9′‐dimethyl‐9H,9′H‐1,1′‐bipyrido[3,4‐b] indole (4j)
(yield of 71%) MS‐ESI, m/z 641.38 [M + Na]+. HR‐MS‐
EI m/z calcd for C40H50N4O2 [M + H]+ 619.4005, found:
1
619.4012. H NMR (600 MHz, CDCl3) δ 8.29 (s, 1 H),
8.18 (d, J = 7.8 Hz, 1 H), 7.51 (t, J = 7.7 Hz, 1 H), 7.28
(d, J = 8.3 Hz, 1 H), 7.23 (t, J = 7.5 Hz, 1 H), 4.94 (s, 2
H), 3.16 (s, 3 H), 2.92 (t, J = 5.6 Hz, 1 H), 1.90 (dp, J =
13.2, 6.6 Hz, 2 H), 0.96 (dd, J = 40.1, 6.7 Hz, 12 H). 13C
NMR (151 MHz, CDCl3) δ 147.81, 142.90, 139.61,
135.23, 131.00, 128.45, 121.82, 121.22, 119.54, 111.91,
109.44, 91.36, 76.77, 31.77, 30.98, 20.43.
3,3′‐bis((cyclopentyloxy)methyl)‐9,9′‐dimethyl‐
9H,9′H‐1,1′‐bipyrido[3,4‐b]indole (4k) (yield of 62%)
MS‐ESI, m/z 581.28 [M + Na]+. HR‐MS‐EI m/z calcd
1
for C36H38N4O2 [M + H]+ 559.3063, found: 559.3073. H
NMR (600 MHz, CDCl3) δ 8.27 (s, 1 H), 8.24 (d, J = 7.8
Hz, 1 H), 7.59 (t, J = 7.7 Hz, 1 H), 7.36 (d, J = 8.3 Hz, 1
H), 7.30 (d, J = 7.2 Hz, 1 H), 4.87 (s, 2 H), 4.19 to 4.17
(m, 1 H), 3.24 (s, 3 H), 1.81 (ddd, J = 6.7, 5.4, 4.8 Hz, 8
H). 13C NMR (151 MHz, CDCl3) δ 147.33, 142.91,
139.80, 135.31, 131.04, 128.52, 121.81, 121.14, 119.64,
112.26, 109.48, 81.62, 72.08, 32.48, 31.81, 23.70.
3,3′‐bis (isobutoxymethyl)‐9,9′‐dimethyl‐9H,9′H‐
1,1′‐bipyrido[3,4‐b]indole (4g) (yield of 87%) MS‐ESI,
m/z 557.28 [M + Na]+. HR‐MS‐EI m/z calcd for
C34H38N4O2 [M + H]+ 535.3058, found: 535.3073. 1H
NMR (600 MHz, CDCl3) δ 8.21 (s, 1 H), 8.16 (d, J = 7.9
Hz, 1 H), 7.51 (t, J = 7.7 Hz, 1 H), 7.29 (d, J = 8.3 Hz, 1
H), 7.23 (t, J = 7.5 Hz, 1 H), 4.81 (d, J = 4.3 Hz, 2 H),
3.35 (d, J = 6.7 Hz, 2 H), 3.17 (s, 3 H), 1.95 (td, J =
13.4, 6.7 Hz, 1 H), 1.23 to 1.15 (m, 2 H), 0.93 (d, J = 6.7
Hz, 6 H). 13C NMR (151 MHz, CDCl3) δ 145.98, 141.91,
138.78, 134.36, 130.04, 127.57, 120.74, 120.09, 118.68,
111.39, 108.49, 76.88, 73.24, 30.77, 27.62, 18.50.
3,3′‐bis((neopentyloxy)methyl)‐9,9′‐dimethyl‐
9H,9′H‐1,1′‐bipyrido[3,4‐b]indole (4l) (yield of 86%)
MS‐ESI, m/z 585.32 [M + Na]+. HR‐MS‐EI m/z calcd
1
for C36H42N4O2 [M + H]+ 563.3368, found: 563.3386. H
NMR (600 MHz, CDCl3) δ 8.28 (s, 1 H), 8.24 (d, J = 7.9
Hz, 1 H), 7.59 (t, J = 7.6 Hz, 1 H), 7.36 (d, J = 8.3 Hz, 1