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Organic & Biomolecular Chemistry
Page 6 of 9
DOI: 10.1039/C8OB01270A
ARTICLE
J = 8.0 Hz, 2H); 7.56-7.58 (m, 1H); C NMR (100 MHz, CDCl
Journal Name
1
3
3
): δ 2H), 7.04-7.06 (m, 2H), 7.43 (dd, J = 6.6 Hz, J = 2.2 Hz, 2H), 7.49
1
3
2
0.5, 23.9, 25.8, 52.4, 98.8, 103.6, 112.5, 112.9, 116.6, 117.6, (d, J = 8.8 Hz, 1H); C NMR (100 MHz, CDCl
3
): δ24.1, 26.1,
+
136.8, 144.0, 149.0, 149.4, 158.7; HRMS (m/z): [M+H] calcd for 53.1, 55.4, 103.7, 114.3, 116.8, 118.9, 119.4, 128.3, 132.3,
+
C
19
H
21
N
2
: 277.1699; found: 277.1692.
134.5, 146.2, 157.2, 160; HRMS (m/z): [M+H] calcd for
O: 293.1648; found: 293.1642.
3
3e): Colorless liquid; yield: 66%; H NMR (400 MHz, CDCl ): δ 3',4'-Dimethoxy-3-(pyrrolidin-1-yl)-[1,1'-biphenyl]-4-
2'-Methoxy-3-(piperidin-1-yl)-[1,1'-biphenyl]-4-carbonitrile
19 21 2
C H N
1
(
1
1
3
7
.57-1.61 (m, 2H), 1.74-1.80 (m, 4H), 3.18 (t, J = 4.8 Hz, 4H), carbonitrile (3l): Colorless liquid; yield: 80%; H NMR (400
.81 (s, 3H), 6.97-7.04 (m, 2H), 7.18 (d, J = 7.6 Hz, 2H), 7.24- MHz, CDCl ): δ 2.00 (t, J = 6.6 Hz, 4H), 3.64 (t, J = 6.6 Hz, 4H),
3.90 (s, 3H), 3.92 (s, 3H), 6.73 (d, J = 2.0 Hz, 1H), 6.81 (d, J =
): δ 24.1, 26.1, 53.1, 55.6, 104.0, 111.3, 10.0 Hz, 1H),6.91 (d, J = 7.6 Hz, 1H), 7.04 (d, J = 2.0Hz, 1H ),
3
1
3
.28 (m, 1H), 7.33-7.37 (m, 1H), 7.18 (d, J = 7.6 Hz, 1H);
C
NMR (100 MHz, CDCl
3
1
3
1
1
2
2
18.9, 119.9, 120.9, 122.4, 129.3, 129.6, 130.5, 133.6, 144.1, 7.09 (d, J = 2.0Hz, 1H), 7.45 (d, J = 7.6 Hz,1H); C NMR (100
+
56.3, 156.5; HRMS (m/z): [M+H] calcd for
C
19
H
21
N
2
O: MHz, CDCl
3
): δ 25.7, 49.9, 56.0, 92.9, 110.5, 111.4, 112.3,
115.0, 119.7, 122.1, 133.3, 136.0, 146.1, 149.2, 149.5, 150.3;
93.1648; found: 293.1640.
+
21 2 2
'-Methoxy-3-morpholino-[1,1'-biphenyl]-4-carbonitrile (3f): HRMS (m/z): [M+H] calcd for C19H N O : 309.1598; found:
1
3
Colorless liquid; yield: 68%; H NMR (400 MHz, CDCl ): δ 3.24 309.1598.
(
t, J = 4.6 Hz, 4H), 3.83 (s, 3H), 3.91 (t, J = 4.6 Hz, 4H), 7.00-7.07 4'-Fluoro-3-(piperidin-1-yl)-[1,1'-biphenyl]-4-carbonitrile
1
(m, 2H), 7.22-7.28 (m, 3H), 7.30-7.38 (m, 1H), 7.60 (d, J = 7.6 (3m): Colorless liquid; yield: 74%; H NMR (400 MHz, CDCl
3
): δ
1
3
3
Hz, 1H); C NMR (100 MHz, CDCl ): δ 51.9, 55.6, 67.0, 104.2, 1.57-1.63 (m, 2H), 1.75-1.81 (m, 4H), 3.21 (t, J = 5.2 Hz, 4H),
1
3
1
1
2
2
11.3, 118.6, 119.8, 121.0, 123.5, 129.0, 129.8, 130.5, 133.8, 7.07-7.14 (m, 4H), 7.50-7.57 (m, 3H); C NMR (100 MHz,
+
44.5, 155.1, 156.3; HRMS (m/z): [M+H] calcd for C18
H
19
N
2
O
2
:
3
CDCl ): δ 23.9, 26.0, 53.1, 104.3, 115.9, 117.3, 118.6, 119.8,
95.1441; found: 295.1433.
'-Methoxy-3-(pyrrolidin-1-yl)-[1,1'-biphenyl]-4-carbonitrile
128.9, 134.7, 136.0, 145.6, 156.9, 163.0; HRMS (m/z):
+
[M+H] calcd for C18
2
H18FN : 281.1449; found: 281.1442.
1
(3g): Colorless liquid; yield: 62%; H NMR (400 MHz, CDCl
3
): δ 4'-Chloro-3-(piperidin-1-yl)-[1,1'-biphenyl]-4-carbonitrile (3n):
1
1
3
.99 (t, J = 3.0 Hz, 4H), 3.66 (t, J = 3.0 Hz, 4H), 3.81 (s, 3H), 6.77 Colorless liquid; yield: 78%; H NMR (400 MHz, CDCl ): δ 1.51-
(
s, 1H), 6.81 (d, J = 8.2 Hz, 1H), 6.98-7.03 (m, 2H), 7.25-7.35 (m, 1.58 (m, 2H), 1.70-1.76 (m, 4H), 3.15 (t, J = 5.2 Hz, 4H), 7.03-
1
3
2
4
1
H), 7.45 (d, J = 8.2 Hz, 1H); C NMR (100 MHz, CDCl
9.8, 55.5, 92.8, 111.2, 115.3, 117.7, 120.8, 121.7, 129.4, J = 8.8 Hz, 1H); C NMR (100 MHz, CDCl
29.8, 130.4, 135.1, 143.8, 149.9, 156.4; HRMS (m/z): 104.3, 118.4, 120.4, 127.2, 128.5, 128.6, 129.0, 129.2, 134.8,
3
): δ 25.7, 7.05 (m, 2H), 7.34-7.37 (m, 2H), 7.41 (d, J = 8.8 Hz, 2H), 7.52 (d,
1
3
3
): δ 23.7, 25.8, 53.3,
+
+
[
M+H] calcd for C18
Methyl 4'-methoxy-3-(methylthio)-[1,1'-biphenyl]-4- 297.1153; found: 297.1150.
carboxylate (3h): Colorless liquid; yield: 58%; H NMR (400 4'-Bromo-3-(piperidin-1-yl)-[1,1'-biphenyl]-4-carbonitrile (3o):
H
19
N
2
O: 279.1492; found: 279.1484.
2
145.5, 154.7; HRMS (m/z): [M+H] calcd for C18H18ClN :
1
1
MHz, CDCl
=
1
3
): δ 2.50 (s, 3H), 3.84 (s, 3H), 3.91 (s, 3H), 6.90 (d, J Off white solid; yield: 80%;Melting Point: 120-122 °C; H NMR
): δ 1.51-1.55 (m, 2H), 1.72-1.75 (m, 4H), 3.16
(t, J = 5.4 Hz, 4H), 7.03-7.05 (m, 2H), 7.35 (d, J = 8.0 Hz,2H),
8.8 Hz, 2H), 7.29 (dd, J = 8.4 Hz, J = 1.6 Hz, 1H), 7.37 (d, J = (400 MHz, CDCl
3
.6 Hz, 1H); 7.53 (d, J = 8.8 Hz, 2H), 8.02 (d, J = 8.4 Hz, 1H);
1
3
C
1
3
NMR (100 MHz, CDCl
3 3
): δ 15.6, 52.0, 55.4, 114.4, 121.9, 122.4, 7.51-7.54 (m, 3H); C NMR (100 MHz, CDCl ): δ 24.0, 26.1,
1
24.6, 128.4, 131.8, 132.4, 143.8, 144.9, 159.9, 166.7; HRMS 53.1, 104.6, 117.1, 118.6, 119.5, 122.8, 128.8, 132.1, 134.7,
+
+
(m/z): [M+H] calcd for C16
H
17
O
3
S: 289.0893; found: 289.0886.
2
138.9, 145.4, 157.2; HRMS (m/z): [M+H] calcd for C18H18BrN :
4
'-Methoxy-3-(methylthio)-[1,1'-biphenyl]-4-carbonitrile (3i): 341.0648; found: 341.0644.
1
Colorless liquid; yield: 60%; H NMR (400 MHz, CDCl
s, 3H), 3.85 (s, 3H), 6.99 (d, J = 8.8 Hz, 2H), 7.35 (dd, J = 8.0 Hz, (3p): Colorless liquid; yield: 75%; H NMR (400 MHz, CDCl
J = 1.4 Hz, 1H), 7.43 (d, J = 1.4 Hz, 1H), 7.50 (d, J = 8.8 Hz, 2H), 1.71-1.72 (m, 6H), 2.80-2.82 (m, 2H), 2.87-2.89 (m, 2H), 3.21
3
): δ 2.60 1-(Piperidin-1-yl)-9,10-dihydrophenanthrene-2-carbonitrile
1
(
3
): δ
1
3
7
1
1
2
4
.60 (d, J = 8.0 Hz, 1H); C NMR (100 MHz, CDCl
09.6, 114.5, 117.2, 123.6, 124.5, 128.4, 131.5, 133.8, 143.8, (m, 1H); C NMR (100 MHz, CDCl
45.6, 160.3; HRMS (m/z): [M+H] calcd for C15
56.0791; found: 256.0785.
3
): δ 15.9, 55.4, (brs, 4H), 7.25-7.32 (m, 3H), 7.47 (d, J = 2.4 Hz, 2H ), 7.66-7.68
1
3
3
): δ 23.3, 24.1, 26.7, 28.5,
+
H14NOS: 52.2, 106.6, 119.7, 119.9, 124.6, 127.1, 127.9, 128.6, 132.6,
+
133.9, 135.6, 137.8, 140.3, 153.6; HRMS (m/z): [M+H] calcd for
'-Methoxy-3-(pyrrolidin-1-yl)-[1,1'-biphenyl]-4-carbonitrile
C
20
H
21
N
2
: 289.1699; found: 289.1697.
1
(3j): Colorless liquid; yield: 76%; H NMR (400 MHz, CDCl
3
): δ 7-Methoxy-1-(piperidin-1-yl)-9,10-dihydrophenanthrene-2-
1
1
6
.94 (t, J = 6.2 Hz, 4H), 3.58 (t, J = 6.2 Hz, 4H), 3.77 (s, 3H), carbonitrile (3q): Colorless liquid; yield: 76%; H NMR (400
.70 (s, 1H), 6.76 (d, J = 8.0Hz, 1H), 6.89 (d, J = 8.8 Hz, 2H), 7.39 MHz, CDCl ): δ 1.70 (brm, 2H), 2.77 (t, J = 4.0 Hz, 2H), 2.86 (t, J
3
1
3
(
d, J = 8.0 Hz, 1H), 7.43 (d, J = 8.8 Hz, 2H); C NMR (100 MHz, = 4.0 Hz, 2H), 3.20 (brs, 4H), 3.83 (s, 3H), 6.78 (d, J = 2.0 Hz, 1H
CDCl ): δ 25.7, 49.9, 55.3, 92.7, 112.1, 114.2, 114.9, 121.6, ), 6.83 (dd, J = 8.4 Hz, J = 2.0 Hz, 1H), 7.39-7.44 (m, 2H), 7.59 (d,
28.2, 132.7, 136.0, 145.8, 150.2, 159.8; HRMS (m/z): J = 8.4 Hz, 1H); C NMR (100 MHz, CDCl
3
1
3
1
3
): δ 23.3, 24.1, 26.8,
+
[M+H] calcd for C18
H
19
N
2
O: 279.1492; found: 279.1484.
28.9, 52.2, 55.3, 105.7, 112.5, 113.2, 119.3, 119.8, 126.0,
4
'-Methoxy-3-(piperidin-1-yl)-[1,1'-biphenyl]-4-carbonitrile
126.7, 132.6, 134.6, 139.6, 140.3, 153.6, 160.0; HRMS (m/z):
1
+
(3k): Colorless liquid; yield: 80%; H NMR (400 MHz, CDCl
3
): δ [M+H] calcd for C21
H
23
N
2
O: 319.1805; found: 319.1802.
1
.54 (t, J = 6.0 Hz, 2H), 1.72 (dd, J = 11 Hz, J = 6.0 Hz, 4H), 3.15 2-(Piperidin-1-yl)-4-(thiophen-2-yl)benzonitrile (3r): Colorless
1
3
(t, J = 6.0 Hz, 4H), 3.79 (s, 3H), 6.91 (dd, J = 6.6 Hz, J = 2.2 Hz, liquid; yield: 82%; H NMR (400 MHz, CDCl ): δ 1.61-1.63 (m,
6
| J. Name., 2012, 00, 1-3
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