Page 5 of 8
The Journal of Organic Chemistry
6.87 (d, J = 4.9 Hz, 1H), 2.40 (s, 3H); 13C{1H} NMR (75 MHz,
C12H10BrN2O [M+H]+ 276.9971, found 276.9970.
3-Methoxy-N-(pyridin-2-yl)benzamide
(15).19
1
2
3
4
5
6
7
8
White
Chloroform-d): δ 166.0, 151.8, 150.1, 147.6, 134.6, 132.3,
128.9, 127.4, 121.2, 114.9, 21.5; HRMS (ESI-TOF) m/z: calcd
for C13H13N2O [M+H]+ 213.1022, found 213.1019.
semisolid; 106.9 mg, 78% yield; 1H NMR (300 MHz,
Chloroform-d): δ 9.03 (s, 1H), 8.39 (d, J = 8.8 Hz, 1H), 8.20 (d,
J = 3.5 Hz, 1H), 7.75 (t, J = 7.9 Hz, 1H), 7.48-7.45 (m, 2H),
7.36 (t, J = 7.8 Hz, 1H), 7.10-7.02 (m, 2H), 3.84 (s, 3H); 13C{1H}
NMR (75 MHz, Chloroform-d): δ 165.9, 160.0, 151.8, 147.9,
138.6, 135.9, 129.9, 120.0, 119.2, 118.7, 114.4, 112.5, 55.5;
HRMS (ESI-TOF) m/z: calcd for C13H13N2O2 [M+H]+
229.0972, found 229.0975.
N-(5-Methylpyridin-2-yl)benzamide (23).19 Yellow solid;
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86.6 mg, 68% yield; m.p. 89-92 C; H NMR (300 MHz,
Chloroform-d): δ 8.88 (s, 1H), 8.29 (d, J = 8.5 Hz, 1H), 8.00 (s,
1H), 7.91 (d, J = 7.3 Hz, 2H), 7.57-7.52 (m, 2H), 7.49-7.45 (m,
2H), 2.28 (s, 3H); 13C{1H} NMR (75 MHz, Chloroform-d): δ
166.1, 149.7, 147.8, 139.1, 134.6, 132.1, 129.2, 128.7, 127.4,
113.9, 17.9; HRMS (ESI-TOF) m/z: calcd for C13H13N2O
[M+H]+ 213.1022, found 213.1018.
9
2,4-Dimethoxy-N-(pyridin-2-yl)benzamide (16). Yellow
o
1
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
solid; 74.4 mg, 48% yield; m.p. 148-151 C; H NMR (300
MHz, Chloroform-d): δ 10.26 (s, 1H), 8.42 (d, J = 8.3 Hz, 1H),
8.32-8.23 (m, 2H), 7.72 (t, J = 7.9 Hz, 1H), 7.04-7.00 (m, 1H),
6.65 (d, J = 8.8 Hz, 1H), 6.53 (s, 1H), 4.05 (s, 3H), 3.87 (s, 3H);
13C{1H} NMR (75 MHz, Chloroform-d): δ 164.2, 163.5, 159.0,
152.3, 148.0, 138.3, 134.3, 119.5, 114.8, 114.3, 105.8, 98.7,
56.3, 55.7; HRMS (ESI-TOF) m/z: calcd for C14H15N2O3
[M+H]+ 259.1077, found 259.1077.
N-(6-Methylpyridin-2-yl)benzamide (24).19 Yellow solid;
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29.3 mg, 23% yield; m.p. 108-110 C; H NMR (300 MHz,
Chloroform-d): δ 8.70 (s, 1H), 8.19 (d, J = 8.3 Hz, 1H), 7.93-
7.90 (m, 2H), 7.64 (t, J = 7.9 Hz, 1H), 7.57-7.52 (m, 1H), 7.49-
7.44 (m, 2H), 6.91 (d, J = 7.4 Hz, 1H), 2.42 (s, 3H); 13C{1H}
NMR (75 MHz, Chloroform-d): δ 165.8, 157.0, 150.9, 138.9,
134.4, 132.3, 128.9, 127.3, 119.6, 111.1, 24.1; HRMS (ESI-
TOF) m/z: calcd for C13H13N2O [M+H]+ 213.1022, found
213.1020.
2,4-Dichloro-N-(pyridin-2-yl)benzamide (17).20 White solid;
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92.8 mg, 58% yield; m.p. 124-126 C; H NMR (300 MHz,
Chloroform-d): δ 10.14 (s, 1H), 8.36 (d, J = 8.3 Hz, 1H), 7.77-
7.68 (m, 2H), 7.58 (d, J = 8.2 Hz, 1H), 7.39 (d, J = 2.0 Hz, 1H),
7.32-7.27 (m, 1H), 6.97-6.93 (m, 1H); 13C{1H} NMR (75 MHz,
Chloroform-d): δ 164.6, 151.5, 147.3, 138.8, 137.1, 134.1,
132.1, 130.7, 130.2, 127.6, 120.2, 114.9; HRMS (ESI-TOF)
m/z: calcd for C12H9Cl2N2O [M+H]+ 267.0086, found 267.0082.
N-(4-Methoxypyridin-2-yl)benzamide (25).21 White solid;
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87.7 mg, 64% yield; m.p. 60-63 C; H NMR (300 MHz,
Chloroform-d): δ 9.90 (s, 1H), 8.08 (t, J = 3 Hz, 1H), 7.93-7.90
(m, 2H), 7.77-7.72 (m, 1H), 7.56-7.51 (m, 1H), 7.47-7.42 (m,
2H), 6.53-6.51 (m, 1H), 3.88 (s, 3H); 13C{1H} NMR (75 MHz,
Chloroform-d): δ 167.6, 166.7, 153.7, 148.4, 134.6, 132.2,
128.8, 127.6, 107.9, 99.1, 55.5; HRMS (ESI-TOF) m/z: calcd
for C13H13N2O2 [M+H]+ 229.0972, found 229.0972.
2,4-Dichloro-5-fluoro-N-(pyridin-2-yl)benzamide
(18).
White solid; 100.9 mg, 59% yield; m.p. 90-92 oC; 1H NMR (300
MHz, Chloroform-d): δ 9.80 (s, 1H), 8.33 (d, J = 8.4 Hz, 1H),
7.92-7.90 (m, 1H), 7.80-7.74 (m, 1H), 7.52-7.45 (m, 2H), 7.05-
6.99 (m, 1H); 13C{1H} NMR (75 MHz, Chloroform-d): δ 163.2,
156.8 (d, J = 252.3 Hz), 151.3, 147.3, 139.9, 135.1 (d, J = 5.9
Hz), 132.0, 126.5, 124.5 (d, J = 19.0 Hz), 120.5, 117.7 (d, J =
24.0 Hz), 115.0; HRMS (ESI-TOF) m/z: calcd for
C12H8Cl2FN2O [M+H]+ 284.9992, found 284.9987.
N-(3-Fluoropyridin-2-yl)benzamide (26).22 Yellow solid;
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54.5 mg, 42% yield; m.p. 97-99 C; H NMR (300 MHz,
Chloroform-d): δ 8.92 (s, 1H), 8.17-8.15 (m, 1H), 7.93 (d, J =
7.5 Hz, 2H), 7.56-7.41 (m, 4H), 7.18-7.12 (m, 1H); 13C{1H}
NMR (75 MHz, Chloroform-d): δ 165.6, 151.9 (d, J = 260.4
Hz), 143.7 (d, J = 5.5 Hz), 140.4 (d, J = 12.6 Hz), 133.6, 132.5,
128.8, 127.8, 124.8 (d, J = 18.1 Hz), 122.3 (d, J = 2.7 Hz);
HRMS (ESI-TOF) m/z: calcd for C12H10FN2O [M+H]+
217.0772, found 217.0773.
N-(Pyridin-2-yl)thiophene-2-carboxamide (19).19 White
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soild; 91.9 mg, 75% yield; m.p. 118-120 C; H NMR (300
MHz, Chloroform-d): δ 9.11 (s, 1H), 8.32 (d, J = 8.4 Hz, 1H),
8.21 (dd, J = 5.0, 1.9 Hz, 1H), 7.77-7.64 (m, 2H), 7.55 (d, J =
4.7 Hz, 1H), 7.09 (t, J = 4.5 Hz, 1H), 7.05-7.01 (m, 1H); 13C{1H}
NMR (75 MHz, Chloroform-d): δ 160.3, 151.5, 147.8, 139.1,
138.6, 131.7, 129.1, 128.0, 120.0, 114.6; HRMS (ESI-TOF)
m/z: calcd for C10H9N2OS [M+H]+ 205.0430, found 205.0426.
N-(Pyridin-2-yl)furan-2-carboxamide (20).19 White solid;
N-(Pyridin-2-yl)acetamide (27).23 Yellow solid; 27.8 mg, 32%
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yield; m.p. 57-59 C; H NMR (300 MHz, Chloroform-d): δ
10.01 (s, 1H), 8.29-8.26 (m, 2H), 7.72 (t, J = 9 Hz, 1H), 7.05 (t,
J = 6 Hz, 1H), 2.21 (s, 3H); 13C{1H} NMR (75 MHz,
Chloroform-d): δ 169.3, 152.1, 147.3, 138.5, 119.6, 114.7, 24.5;
HRMS (ESI-TOF) m/z: calcd for C7H9N2O [M+H]+ 137.0709,
found 137.0710.
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61.0 mg, 54% yield; m.p. 81-84 C; H NMR (300 MHz,
Chloroform-d): δ 8.91 (s, 1H), 8.34-8.31 (m, 2H), 7.77-7.70 (m,
1H), 7.52 (s, 1H), 7.28 (m, 1H), 7.09-7.05 (m, 1H), 6.58-6.55
(m, 1H); 13C{1H} NMR (75 MHz, Chloroform-d): δ 156.3,
151.1, 148.1, 147.4, 144.8, 138.5, 120.0, 116.0, 114.3, 112.7;
HRMS (ESI-TOF) m/z: calcd for C10H9N2O2 [M+H]+ 189.0659,
found 189.0657.
N-(Pyridin-2-yl)isobutyramide (28).11 White solid; 44.3 mg,
45% yield; m.p. 54-56 oC; 1H NMR (300 MHz, Chloroform-d):
δ 8.27-8.22 (m, 2H), 8.10 (s, 1H), 7.70 (t, J = 7.7 Hz, 1H), 7.05-
7.01 (m, 1H), 2.55 (p, J = 6.9 Hz, 1H), 1.27 (d, J = 4.5 Hz, 6H);
13C{1H} NMR (75 MHz, Chloroform-d): δ 175.8, 151.7, 147.8,
138.6, 119.8, 114.2, 36.8, 19.6; HRMS (ESI-TOF) m/z: calcd
for C9H13N2O [M+H]+ 165.1022, found 165.1019.
N-(3-Methylpyridin-2-yl)benzamide (21).19 Yellow semisolid;
99.3 mg, 78% yield; 1H NMR (300 MHz, Chloroform-d): δ 9.71
(s, 1H), 8.14-8.12 (m, 1H), 7.92 (d, J = 7.3 Hz, 2H), 7.55 (d, J
= 7.6 Hz, 1H), 7.48 (t, J = 7.3 Hz, 1H), 7.40-7.35 (m, 2H), 7.09-
7.05 (m, 1H), 2.28 (s, 3H); 13C{1H} NMR (75 MHz,
Chloroform-d): δ 166.4, 150.2, 145.3, 140.1, 134.1, 132.0,
129.7, 128.5, 127.8, 121.8, 18.4; HRMS (ESI-TOF) m/z: calcd
for C13H13N2O [M+H]+ 213.1022, found 213.1024.
N-(Pyridin-2-yl)cyclohexanecarboxamide (29).12 White solid;
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41.7 mg, 34% yield; m.p. 85-87 C; H NMR (300 MHz,
Chloroform-d): δ 8.35 (s, 1H), 8.25-8.22 (m, 2H), 7.69 (t, J =
7.8 Hz, 1H), 7.02 (t, J = 6.1 Hz, 1H), 2.25 (t, J = 11.9 Hz, 1H),
1.95 (d, J = 12.5 Hz, 2H), 1.84-1.80 (m, 2H), 1.69-1.67 (m, 1H),
1.53 (q, J = 12.1 Hz, 2H), 1.35-1.23 (m, 3H); 13C{1H} NMR (75
MHz, Chloroform-d): δ 175.1, 151.8, 147.7, 138.6, 119.7, 114.3,
46.5, 29.6, 25.74, 25.70; HRMS (ESI-TOF) m/z: calcd for
C12H17N2O [M+H]+ 205.1335, found 205.1335.
N-(4-Methylpyridin-2-yl)benzamide (22).19 Yellow solid;
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104.4 mg, 82% yield; m.p. 108-110 C; H NMR (300 MHz,
Chloroform-d): δ 8.94 (s, 1H), 8.25 (s, 1H), 8.04 (d, J = 5.1 Hz,
1H), 7.94-7.91 (m, 2H), 7.59-7.53 (m, 1H), 7.50-7.45 (m, 2H),
N-(Pyridin-2-yl)cyclopentanecarboxamide (30). White solid;
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44.5 mg, 39% yield; m.p. 86-88 C; H NMR (300 MHz,
Chloroform-d): δ 8.26-8.21 (m, 2H), 8.09 (s, 1H), 7.69 (t, J =
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