Org aP nl ei ca s &e dB oi on mo to al ed cj uu sl at rm Ca hr ge imn si stry
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ARTICLE
Journal Name
2
0
1
1
30.2, 129.5, 128.9, 128.5, 126.1, 125.2, 122.4, 120.4, 119.5, 114.2, 2‐(Naphthalen‐2‐yl)‐3‐phenyl‐1H‐indole (2h).
10.8, 55.3. HRMS (ESI) calculated for C H NO [M+H] : 300.1388,
24 18
+
DOI: 10.1039/C6OB00423G
The product was obtained following the general procedure. Yield:
3%. H NMR (400 MHz, CDCl ): δ 8.28 (br 1H), 7.92 (s, 1H), 7.80–
found: 300.1385.
1
9
3
2
‐(2,5‐Dimethoxyphenyl)‐3‐phenyl‐1H‐indole (2b).
7.73 (m, 2H), 7.73–7.68 (m, 2H), 7.47–7.40 (m, 6H), 7.38–7.33 (m,
1
3
2H), 7.30–7.23 (m, 2H), 7.16 (t, J = 7.6 Hz, 1H). C NMR (100 MHz,
The product was obtained following the general procedure. Yield:
CDCl ): δ 136.2, 135.1, 134.1, 133.5, 132.7, 130.4, 130.3, 128.9,
3
1
74%. H NMR (400 MHz, CDCl ): δ 9.22 (br, 1H), 7.64 (d, J = 8.0 Hz,
3
128.6, 128.2, 128.1, 127.8, 126.7, 126.5, 126.4, 126.3, 122.9, 120.6,
1H), 7.47–7.43 (m, 2H), 7.42–7.35 (m, 3H), 7.29–7.19 (m, 2H), 7.11
+
1
3
19.8, 115.6, 111.0. HRMS (ESI) calculated for C H N, [M+H] :
20.1434, found: 320.1446.
2
4 18
(
ddd, J = 8.0, 7.1, 1.0 Hz, 1H), 6.89 (d, J = 9.0 Hz, 1H), 6.80 (d, J = 3.2
1
3
Hz, 1H), 6.76 (dd, J = 8.9, 3.1 Hz, 1H), 3.80 (s, 3H), 3.36 (s, 3H).
C
NMR (100 MHz, CDCl ): δ 153.5, 150.9, 136.0, 135.4, 131.1, 130.4, 2‐(6‐Methoxynaphthalen‐2‐yl)‐3‐phenyl‐1H‐indole (2i).
3
1
1
28.6, 128.0, 126.3, 122.6, 121.5, 120.0, 119.4, 116.1, 115.9, 115.2,
The product was obtained following the general procedure. Yield:
13.4, 110.9, 56.6, 55.3. HRMS (ESI) calculated for C H NO ,
2
2
20
2
1
+
73%. H NMR (400 MHz, CDCl ): δ 8.20 (br, 1H), 7.80 (s, 1H), 7.69 (t,
[
M+H] : 330.1489, found: 330.1482.
‐Phenyl‐2‐(3,4,5‐trimethoxyphenyl)‐1H‐indole (2c).
The product was obtained following the general procedure. Yield:
3
J = 7.6 Hz, 1H), 7.63–7.53 (m, 2H), 7.44 (t, J = 7.5 Hz, 2H), 7.39–7.30
3
(m, 4H), 7.29–7.19 (m, 2H), 7.17–7.08 (m, 2H), 7.07–7.02 (m, 1H),
1
3
3
1
.86 (s, 3H). C NMR (100 MHz, CDCl ): δ 158.1, 136.1, 135.2, 134.4,
3
33.9, 130.3, 129.6, 128.9(4), 128.8(9), 128.6, 128.1, 127.0, 126.6,
1
7
1
6
1
1
6%. H NMR (400 MHz, CDCl ): δ 8.34 (br, 1H), 7.64 (d, J = 8.0 Hz,
3
126.3, 122.7, 120.5, 119.9, 119.3, 115.0, 111.0, 105.8, 55.4. HRMS
H), 7.50–7.33 (m, 5H), 7.32–7.20 (m, 2H), 7.15 (t, J = 7.6 Hz, 1H),
+
(
ESI) calculated for C H NO [M+H] : 350.1539, found: 350.1531.
25 20
1
3
.62 (s, 2H), 3.87 (s, 3H), 3.66 (s, 6H). C NMR (100 MHz, CDCl ): δ
3
19
53.3, 137.7, 135.8, 135.2, 134.0, 130.4, 128.9, 128.5, 128.0, 127.3, 2‐([1,1’‐Biphenyl]‐4‐yl)‐3‐phenyl‐1H‐indole (2j).
26.4, 122.7, 120.5, 119.6, 115.2, 110.9, 105.3, 104.9, 61.0, 55.9.
+
The product was obtained following the general procedure. Yield:
HRMS (ESI) calculated for C H NO , [M+H] : 360.1600, found:
3
2
3
22
3
1
8
9%. H NMR (400 MHz, CDCl ): δ 8.27 (br, 1H), 7.76 (d, J = 7.9 Hz,
60.1594.
3
1
H), 7.68–7.63 (m, 2H), 7.63–7.59 (m, 2H), 7.58–7.35 (m, 11H), 7.32
1
3
4
‐(4‐(3‐Phenyl‐1H‐indol‐2‐yl)phenyl)morpholine (2d).
(t, J = 7.6 Hz, 1H), 7.27–7.17 (m, 1H). C NMR (100 MHz, CDCl ): δ
3
1
1
40.4, 140.3, 136.0, 135.2, 133.7, 131.6, 130.3, 128.9(4), 128.9(0),
28.7, 128.5, 127.6, 127.3, 127.9, 126.4, 122.9, 120.6, 119.8, 115.4,
The product was obtained following the general procedure. Yield:
1
8
1
7
3
1
1
9%. H NMR (400 MHz, CDCl ): δ 8.21 (br, 1H), 7.65 (d, J = 8.0 Hz,
+
3
111.0. HRMS (ESI) calculated for C H N [M+H] : 346.1590, found:
26 20
3
H), 7.47–7.32 (m, 7H), 7.30–7.25 (m, 2H), 7.24-7.19 (m, 1H),
.16–7.10 (m, 1H), 6.85 (d, J = 8.4 Hz, 2H), 3.85 (t, J = 4.7 Hz, 4H),
46.1580.
1
3
.18 (t, J = 4.8 Hz, 4H). C NMR (100 MHz, CDCl ): δ 135.8, 135.4, 3‐Phenyl‐2‐(pyren‐2‐yl)‐1H‐indole (2k).
3
34.2, 130.2, 129.0, 128.9, 128.5, 126.0, 122.3, 120.3, 119.4, 115.3,
The product was obtained following the general procedure. Yield:
80%. H NMR (400 MHz, CDCl ): δ 8.20 (br, 1H), 8.13 (d, J = 7.6 Hz,
3
14.0, 110.7, 66.8, 48.8. HRMS (ESI) calculated for C H N O
24 21 2
1
+
[
M+H] : 355.18109, found: 355.1802.
‐(3‐Phenyl‐1H‐indol‐2‐yl)benzonitrile (2e).
The product was obtained following the general procedure. Yield:
1H), 8.08–7.82 (m, 9H), 7.38 (d, J = 8.0 Hz, 1H), 7.34–7.20 (m, 4H),
1
9
13
4
7.10 (t, J = 7.4 Hz, 2H), 7.07–7.00 (m, 1H). C NMR (100 MHz,
CDCl ): δ 136.3, 135.0, 133.8, 131.4, 131.3, 130.9, 129.8, 129.5,
1
3
29.0, 128.4, 128.0, 127.8, 127.7, 127.4, 126.2, 125.8, 125.5, 125.3,
1
2
1
6
3%. H NMR (400 MHz, CDCl ): δ 8.35 (br, 1H), 7.64 (d, J = 7.9 Hz,
H), 7.57 (d, J = 8.2 Hz, 2H), 7.49 (d, J = 8.2 Hz, 2H), 7.47–7.32 (m,
H), 7.29 (t, J = 7.4 Hz, 1H), 7.17 (t, J = 7.6 Hz, 1H). C NMR (100
3
125.2, 125.0, 124.7, 124.6, 122.8, 120.6, 119.9, 117.2, 111.1. HRMS
+
(ESI) calculated for C H N [M+H] : 394.1590, found: 394.1583.
30 20
1
3
2
1
MHz, CDCl ): δ 137.2, 136.4, 134.23, 132.4, 131.6, 130.1, 128.9, 3‐Phenyl‐2‐(thiophen‐2‐yl)‐1H‐indole (2l).
3
1
28.8, 128.3, 127.0, 123.9, 120.9, 120.2, 118.8, 117.6, 111.2, 110.7.
+
The product was obtained following the general procedure. Yield:
HRMS (ESI) calculated for , C H N [M+H] : 292.1235, found:
2
1 15 2
1
6
9%. H NMR (400 MHz, CDCl ): δ 8.17 (br, 1H), 7.55 (d, J = 7.9 Hz,
2
92.1239.
3
1H), 7.52–7.47 (m, 2H), 7.45–7.32 (m, 4H), 7.27–7.19 (m, 2H), 7.14–
(
4‐(3‐Phenyl‐1H‐indol‐2‐yl)phenyl)(pyrrolidin‐1‐yl)methanone (2g). 7.09 (m, 1H), 7.06 (dd, J = 3.6, 1.1 Hz, 1H), 6.97 (dd, J = 5.1, 3.7 Hz,
1
3
1
H). C NMR (100 MHz, CDCl ): δ 135.8, 134.6, 134.5, 130.6, 129.1,
3
The product was obtained following the general procedure. Yield:
1
28.6, 128.3, 127.5, 126.9, 125.4, 125.3, 123.1, 120.6, 119.7, 115.9,
1
8
1
7
2
1
1
0%. H NMR (400 MHz, CDCl ): δ 8.90 (br, 1H), 7.66 (d, J = 8.0 Hz,
+
3
110.8. HRMS (ESI) calculated for C H NS [M+H] : 276.0841, found:
18 14
2
H), 7.48 (d, J = 8.2 Hz, 1H), 7.46–7.33 (m, 8H), 7.33–7.22 (m, 3H),
.15 (t, J = 7.4 Hz, 1H), 3.67 (t, J = 7.0 Hz, 2H), 3.45 (t, J = 6.6 Hz, 2H),
76.0845.
1
3
.00–1.84 (m, 4H). C NMR (100 MHz, DMSO): δ 167.7, 136.2, 2‐(3‐Phenyl‐1H‐indol‐2‐yl)quinoline (2m).
35.8, 135.0, 133.7, 133.1, 129.8, 128.7, 128.0, 127.6, 127.3, 126.3,
The product was obtained following the general procedure. Yield:
27%. H NMR (400 MHz, CDCl ): δ 9.92 (br, 1H), 8.11 (d, J = 8.4 Hz,
3
22.3, 119.8, 118.7, 114.0, 111.5, 48.8, 45.9, 26.0, 23.9. HRMS (ESI)
1
+
calculated for C H N O [M+H] : 367.1805, found: 367.1809.
2
5 23 2
1H), 7.87 (d, J = 8.8 Hz, 1H), 7.75–7.68 (m, 2H), 7.60–7.42 (m, 9H),
4
| J. Name., 2012, 00, 1‐3
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