The Journal of Organic Chemistry
Page 22 of 51
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3
2
H), 3.35 (t, J = 8.3 Hz, CH
2
, 2H), 2.96 (t, J = 8.3 Hz, CH
2
, 2H). C NMR (100 MHz, CDCl ) δ 153.2, 152.6,
3
142.5, 138.4, 131.1, 128.7, 128.0, 127.4, 127.2, 125.9, 124.1, 110.5, 107.1, 107.1, 78.7, 53.8, 53.6, 43.4,
–
1
2
8.6. IR (CH
2
Cl , cm ): 3445, 2845, 1617, 1552, 1497, 1376, 1267, 1146, 1013, 810, 736. Anal. Calcd
2
for C21
20
H N
2
O
3
: C, 72.40; H, 5.79; N, 8.04; found: C, 72.51; H, 5.72; N, 8.15. Rf = 0.67 (EtOAc/Hexane
+
0
1
2
3
4
5
6
7
8
9
0
1
2
3
4
5
6
7
8
9
0
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2
3
4
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6
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9
0
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7
8
9
0
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2
3
4
5
6
7
8
9
0
(1:9), 254 nm). HRMS (APCI-TOF) m/z: [M + H] Calcd for C21
H
21
N
2
O 349.1552; Found 349.1528.
3
(
±)-5-(1-(1-Benzylindolin-5-yl)-2-nitroethyl)-1H-indole (12aj). Compound 12aj was obtained using GP3.
Column chromatography (Acetone/Hexane (2:8)) gave the product as brown oil (1.85 mg, 78% yield).
1H NMR (400 MHz, CDCl
) δ 8.13 (s, NH, 1H), 7.51 (s, =CH, 1H), 7.37 – 7.23 (m, =CH, 6H), 7.20 – 7.15
m, =CH, 1H), 7.08 – 7.03 (m, =CH, 1H), 7.00 – 6.93 (m, =CH, 2H), 6.53 – 4.48 (m, =CH, 1H), 6.42 (d, J =
3
(
7
.9 Hz, =CH, 1H), 5.03 – 4.95 (m, CH
, 2H), 2.91 (t, J = 8.3 Hz, CH , 2H). C NMR (100 MHz, CDCl
29.5, 128.7, 128.3, 128.1, 127.4, 126.7, 125.0, 124.3, 122.3, 119.5, 111.7, 107.1, 102.9, 80.5, 53.9 (2C),
2
, 2H), 4.94 – 4.86 (m, CH, 1H), 4.21 (s, CH
2
, 2H), 3.29 (t, J = 8.3 Hz,
13
CH
2
2
3
) δ 152.0, 138.6, 135.1, 131.8, 131.0,
1
4
C
–1
9.0, 28.7. IR (CH
2
Cl , cm ): 3422, 1614, 1549, 1496, 1377, 1266, 1094, 894, 732. Anal. Calcd for
2
25
H
23
N
3
O
2
: C, 75.55; H, 5.83; N, 10.57; found: C, 75.29; H, 5.99; N, 10.24. Rf = 0.41 (EtOAc/Hexane
+
(3:7), 254 nm). HRMS (APCI-TOF) m/z: [M + H] Calcd for C25
H
24
N
3
O 398.1869; Found 398.1854.
2
(±)-3-(1-(1-Benzylindolin-5-yl)-2-nitroethyl)-1H-indole (12ak). Compound 12ak was obtained using
GP3. Column chromatography (Acetone/Hexane (2:8)) gave the product as brown oil (1.85 mg, 78%
1
yield). H NMR (400 MHz, CDCl
3
) δ 8.03 (s, NH, 1H), 7.49 (d, J = 8.0 Hz, =CH, 1H), 7.35 – 7.23 (m, =CH,
6H), 7.21 – 7.15 (m, =CH, 1H), 7.10 – 6.98 (m, =CH, 4H), 6.41 (d, J = 8.7 Hz, =CH, 1H), 5.10 – 4.97 (m,
CH , 2H), 4.90 – 4.82 (m, CH, 1H), 4.19 (s, CH , 2H) 3.31 – 3.24 (m, CH , 2H), 2.92 – 2.86 (m, CH , 2H).
13C NMR (100 MHz, CDCl
) δ 152.6, 138.4, 136.5, 130.8, 128.5, 128.3, 127.9, 127.2, 126.8, 126.3, 124.0,
122.6, 121.4, 119.8, 119.2, 115.3, 111.3, 106.9, 80.1, 53.7 (2C), 41.2, 28.5. IR (CH
2
2
2
2
3
–
1
2
Cl
2
, cm ): 3419,
3
C
047, 2957, 2913, 2829, 1615, 1548, 1495, 1456, 1378, 1265, 1098, 808, 741. Anal. Calcd for
25
H
23
N
3
O
2
: C, 75.55; H, 5.83; N, 10.57; found: C, 75.31; H, 6.00; N, 10.63. Rf = 0.36 (EtOAc/Hexane
+
(3:7), 254 nm). HRMS (APCI-TOF) m/z: [M + H] Calcd for C25
H
24
N
3
O 398.1869; Found 398.1847.
2
(
dia)-1-Benzyl-2-methyl-5-(2-nitro-1-phenylethyl)indoline (12ba). Compound 12ba was obtained using
GP3. Thin layer chromatography (EtOAc/Hexane (1:9)) gave the product as yellow oil (1.08 mg, 86%
1
yield). H NMR (400 MHz, CDCl
3
) δ 7.53 – 7.31 (m, =CH, 10H), 7.04 (s, =CH, 1H), 6.98 – 6.93 (m, =CH,
, 3H), 4.45 (d, J = 16.0 Hz, B part of AB system,
, 1H), 3.88 – 3.81 (m, CH , 1H), 3.27 – 3.20 (m,
, 3H). C NMR (100 MHz, CDCl ) δ
1
H), 6.39 – 6.37 (m, =CH, 1H), 5.06 – 4.82 (m, CH, CH
2
CH
2
, 1H), 4.28 (d, J = 16.0 Hz, B part of AB system, CH
2
2
13
CH
2
, 1H), 2.75 (dd, J = 15.6, 9.4 Hz, CH , 1H), 1.44 – 1.37 (m, CH
2
3
3
1
1
52.5, 140.6, 139.4, 130.0, 129.2, 128.9, 128.4, 127.9, 127.7, 127.6, 127.3, 127.0, 126.9, 124.0, 123.9,
–1
07.0, 79.9, 61.1, 51.5, 49.0, 37.6, 20.0. IR (CH
Cl
2 2
, cm ): 3061, 3028, 2963, 2925, 2839, 1615, 1551,
2
2
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