6
ACCEPTED MANUSCRIPT
[
7e]
4
.3.35 N-(5-iodoquinolin-8-yl)-4-methoxybenzamide (3dc)
.
8.15 (d, J = 8.5 Hz, 3H), 7.78 (d, J = 8.0 Hz, 2H), 7.68-7.66 (m,
2H), 7.58 (dd, J = 8.5, 4.5 Hz, 1H), 7.50 (t, J = 7.5 Hz, 2H),
o
1
White solid, m.p. 170-171 C, 45% yield (36.4 mg). H NMR
500 MHz, CDCl ) δ 10.67 (s, 1H), 8.82 (dd, J = 4.0, 1.0 Hz,
13
(
7.43-7.40 (m, 1H). C NMR (125 MHz, CDCl ) δ 165.3, 149.0,
3
3
1
H), 8.70 (d, J = 8.5 Hz, 1H), 8.39 (dd, J = 8.5, 1.0 Hz, 1H), 8.12
145.0, 141.0, 140.2, 139.6, 138.6, 135.7, 133.7, 129.9, 129.1,
128.3, 128.0, 127.7, 127.4, 123.4, 118.1, 89.6. HRMS (ESI):
(d, J = 8.0 Hz, 1H), 8.06-8.03 (m, 2H), 7.56 (dd, J = 8.5, 4.0 Hz,
13
+
+
1
H), 7.06-7.03 (m, 2H), 3.90 (s, 3H). C NMR (125 MHz,
calcd for C H IN O ([M + H] ) 451.0302, Found: 451.0304.
22 16 2
CDCl ) δ 165.1, 162.9, 148.9, 140.9, 139.6, 138.6, 135.9, 129.9,
[13]
3
4
.3.43 N-(5-iodoquinolin-8-yl)-2-naphthamide (3lc) . White
1
29.4, 127.4, 123.3, 117.9, 114.2, 89.2, 55.6.
o
1
solid, m.p. 150-151 C, 71% yield (60.2 mg). H NMR (500
MHz, CDCl ) δ 10.78 (s, 1H), 8.77 (d, J = 3.5 Hz, 1H), 8.69 (d, J
= 8.0 Hz, 1H), 8.52 (s, 1H), 8.30 (d, J = 8.5 Hz, 1H), 8.06 (d, J =
8.5 Hz, 2H), 7.98 (d, J = 8.0 Hz, 1H), 7.92 (d, J = 8.5 Hz, 1H),
[
7e]
4
.3.36 4-fluoro-N-(5-iodoquinolin-8-yl)benzamide (3ec)
.
3
o
1
White solid, m.p. 169-170 C, 50% yield (39.2 mg). H NMR
500 MHz, CDCl ) δ 10.65 (s, 1H), 8.80-8.79 (m, 1H), 8.65 (d, J
(
3
=
8.5 Hz, 1H), 8.37 (d, J = 8.5 Hz, 1H), 8.11-8.05 (m, 3H), 7.54
7.86 (d, J = 8.0 Hz, 1H), 7.58-7.53 (m, 2H), 7.47 (dd, J = 8.5, 4.0
13
13
(dd, J = 8.5, 3.0 Hz, 1H), 7.23-7.20 (m, 2H). C NMR (125
Hz, 1H). C NMR (125 MHz, CDCl ) δ 165.3, 148.9 , 140.7,
3
MHz, CDCl ) δ 165.3 (d, J = 251.3 Hz), 164.3, 149.0, 140.9,
139.4, 138.4, 135.6, 135.1, 132.8, 132.1, 129.7, 129.3, 128.8,
128.1, 128.0, 127.9, 126.9, 123.7, 123.2, 118.0, 89.6.
3
CF
1
39.4, 138.5, 135.5, 131.2 (d, JCF = 2.5 Hz), 129.83 (d, JCF = 8.8
Hz), 129.82, 123.4, 118.0, 116.0 (d, JCF = 21.3 Hz), 89.7.
[13]
4
.3.44 N-(5-iodoquinolin-8-yl)propionamide (3mc) . Yellow
[
7e]
o
1
4
.3.37 4-chloro-N-(5-iodoquinolin-8-yl)benzamide (3fc)
.
solid, m.p. 124-125 C, 48% yield (31.3 mg). H NMR (500
MHz, CDCl ) δ 9.80 (s, 1H), 8.75 (d, J = 4.0 Hz, 1H), 8.54 (d, J
= 8.0 Hz, 1H), 8.34 (d, J = 8.5 Hz, 1H), 8.05 (d, J = 8.5 Hz, 1H),
o
1
Yellow solid, m.p. 179-180 C, 78% yield (63.7 mg). H NMR
500 MHz, CDCl ) δ 10.64 (s, 1H), 8.77 (d, J = 4.0 Hz, 1H),
3
(
3
8
8
.63 (d, J = 8.0 Hz, 1H), 8.34 (d, J = 8.5 Hz, 1H), 8.08 (d, J =
7.51 (dd, J = 8.5, 4.0 Hz, 1H), 2.59 (q, J = 7.5 Hz, 2H), 1.33 (t, J
13
13
.0 Hz, 1H), 7.97 (d, J = 8.5 Hz, 2H), 7.54-7.48 (m, 3H).
C
= 7.5 Hz, 3H). C NMR (125 MHz, CDCl ) δ 172.6, 148.8,
3
NMR (125 MHz, CDCl ) δ 164.3, 149.0, 140.9, 139.4, 138.5,
140.8, 139.1, 138.5, 135.7, 129.7, 123.2, 117.9, 89.1, 31.4, 9.8.
3
1
38.4, 135.4, 133.3, 129.8, 129.2, 128.8, 123.4, 118.1, 89.9.
4
.3.45 N-(5-iodoquinolin-8-yl)cyclohexanecarboxamide (3nc)
o 1
[
11]
4
.3.38 2-chloro-N-(5-iodoquinolin-8-yl)benzamide (3gc). Yellow
. Yellow solid, m.p. 112-113 C, 58% yield (44.1 mg). H
o
1
solid, m.p. 181-182 C, 70% yield (57.2 mg). H NMR (500
NMR (500 MHz, CDCl ) δ 9.84 (s, 1H), 8.71 (dd, J = 4.0, 1.0
3
MHz, CDCl ) δ 10.51 (s, 1H), 8.73 (d, J = 4.0, 1H), 8.70 (d, J =
Hz, 1H), 8.52 (d, J = 8.5 Hz, 1H), 8.27 (dd, J = 8.5, 1.5 Hz, 1H),
7.99 (d, J = 8.5 Hz, 1H), 7.45 (dd, J = 8.5, 4.0 Hz, 1H), 2.47-
2.41 (m, 1H), 2.07-2.04 (m, 2H), 1.87-1.84 (m, 2H), 1.72-1.70
3
8
.0, 1H), 8.34 (d, J = 8.5 Hz, 1H), 8.11 (d, J = 8.0 Hz, 1H), 7.81
13
(d, J = 7.5 Hz, 1H), 7.51-7.48 (m, 2H), 7.44-7.37 (m, 2H).
C
13
NMR (125 MHz, CDCl ) δ 164.9, 149.0, 140.8, 139.3, 138.3,
(m, 1H), 1.65-1.57 (m, 2H), 1.40-1.23 (m, 3H). C NMR (125
3
1
1
4
35.6, 135.5, 131.8, 131.3, 130.7, 130.3, 129.8, 127.3, 123.3,
MHz, CDCl ) δ 174.8, 148.7, 140.7, 139.1, 138.3, 135.6, 129.5,
123.1, 117.8, 89.0, 46.9, 29.8, 25.83, 25.79.
3
+
+
18.3, 90.2. HRMS (ESI): calcd for C H ClIN O ([M + H] )
16
11
2
08.9599, Found: 408.9610.
[13]
4
.3.46 N-(5-iodoquinolin-8-yl)-2-phenylacetamide (3oc)
.
[7e]
o
1
4
.3.39 3-chloro-N-(5-iodoquinolin-8-yl)benzamide (3hc)
.
Yellow solid, m.p. 99-100 C, 71% yield (55.1 mg). H NMR
o
1
Yellow solid, m.p. 175-176 C, 73% yield (59.7 mg). H NMR
500 MHz, CDCl ) δ 10.65 (s, 1H), 8.80 (dd, J = 4.0, 1.5 Hz,
(500 MHz, CDCl ) δ 9.89 (s, 1H), 8.62 (d, J = 4.0 Hz, 1H), 8.52
3
(
1
(d, J = 8.5 Hz, 1H), 8.29 (d, J = 8.0 Hz, 1H), 8.02 (d, J = 8.0 Hz,
3
1
3
H), 8.64 (d, J = 8.5 Hz, 1H), 8.36 (dd, J = 8.5, 1.5 Hz, 1H), 8.09
1H), 7.46-7.40 (m, 5H), 7.35-7.33 (m, 1H), 3.88 (s, 2H).
C
(
7
d, J = 8.5 Hz, 1H), 8.02 (t, J = 1.5 Hz, 1H), 7.91-7.90 (m, 1H),
.55-7.53 (m, 2H), 7.47 (t, J = 8.0 Hz, 1H). C NMR (125 MHz,
NMR (125 MHz, CDCl ) δ 169.6, 148.8, 140.7, 139.1, 138.3,
135.4, 134.6, 129.7, 129.6, 129.1, 127.5, 123.2, 117.8, 89.5,
45.5.
3
13
CDCl ) δ 164.0, 149.1, 140.9, 139.3, 138.4, 136.8, 135.3, 135.2,
3
1
32.2, 130.2, 129.8, 127.8, 125.4, 123.4, 118.2, 90.1.
[11]
4
.3.47 N-(5-iodoquinolin-8-yl)furan-2-carboxamide (3pc)
.
[
10]
o
1
4
.3.40 4-bromo-N-(5-iodoquinolin-8-yl)benzamide (3ic)
.
Yellow solid, m.p. 177-178 C, 20% yield (14.6 mg). H NMR
(500 MHz, CDCl ) δ 10.71 (s, 1H), 8.80-8.79 (m, 1H), 8.59 (dd,
J = 8.0, 1.5 Hz, 1H), 8.33 (d, J = 8.5 Hz, 1H), 8.07-8.05 (m, 1H),
7.58 (s, 1H), 7.52-7.50 (m, 1H), 7.21 (d, J = 1.5 Hz, 1H), 6.55-
6.54 (m, 1H). C NMR (125 MHz, CDCl ) δ 156.5, 149.1,
o
1
Yellow solid, m.p. 169-170 C, 60% yield (54.4 mg). H NMR
500 MHz, CDCl ) δ 10.70 (s, 1H), 8.82 (dd, J = 4.0, 1.5 Hz,
3
(
1
3
H), 8.67 (d, J = 8.0 Hz, 1H), 8.40 (dd, J = 8.5, 1.0 Hz, 1H), 8.12
13
(
(
d, J = 8.5 Hz, 1H), 7.94-7.92 (m, 2H), 7.69-7.68 (m, 2H), 7.57
dd, J = 8.5, 4.0 Hz, 1H). C NMR (125 MHz, CDCl ) δ 164.5,
3
13
148.4, 144.8, 140.9, 139.4, 138.4, 135.3, 129.9, 123.4, 118.2,
115.6, 112.7, 89.8.
3
1
1
49.1, 141.1, 139.4, 138.5, 135.4, 133.9, 132.3, 129.9, 129.0,
27.0, 123.4, 118.2, 90.0.
[15]
4
.3.48 N-(4-bromophenyl)benzamide (3qb) . White solid, m.p.
201-202 C, 80% yield (44.1 mg). H NMR (500 MHz,
(CD ) SO) δ 10.37 (s, 1H), 7.95 (d, J = 7.0 Hz, 2H), 7.77 (d, J =
8.5 Hz, 2H), 7.61-7.58 (m, 1H), 7.55-7.52 (m, 4H). C NMR
o
1
4
.3.41
N-(5-iodoquinolin-8-yl)-4-(trifluoromethyl)benzamide
[
13]
o
1
(3jc) . White solid, m.p. 122-123 C, 53% yield (46.9 mg). H
3
2
1
3
NMR (500 MHz, CDCl ) δ 10.71 (s, 1H), 8.78 (d, J = 4.0 Hz,
3
1
=
7
1
3
H), 8.63 (d, J = 8.0 Hz, 1H), 8.35 (d, J = 8.5 Hz, 1H), 8.14 (d, J
8.0 Hz, 2H), 8.08 (d, J = 8.0 Hz, 1H), 7.80 (d, J = 8.0 Hz, 2H),
(125 MHz, (CD ) SO) δ 165.6, 138.5, 134.7, 131.6, 131.3, 128.3,
127.6, 122.2, 115.3.
3
2
13
.53 (dd, J = 8.5, 4.0 Hz, 1H). C NMR (125 MHz, CDCl ) δ
[16]
3
4
.3.49 N-(4-bromonaphthalen-1-yl)benzamide (3rb) . White
64.0, 149.1, 141.0, 139.3, 138.4, 138.2, 135.2, 133.8 (q, JCF
=
o
1
solid, m.p. 236-237 C, 70% yield (45.6 mg). H NMR (500
2.5 Hz), 129.8, 127.9, 126.0 (q, JCF = 3.8 Hz), 123.4, 123.3 (q,
MHz, (CD ) SO) δ 10.52 (s, 1H), 8.19 (d, J = 8.5 Hz, 1H), 8.10-
3
2
JCF = 271.3 Hz), 118.2, 90.2.
8
.07 (m, 3H), 7.94 (d, J = 8.0 Hz, 1H), 7.74 (t, J = 7.5 Hz, 1H),
13
4
.3.42 N-(5-iodoquinolin-8-yl)-[1,1'-biphenyl]-4-carboxamide
7.68-7.63 (m, 2H), 7.58 (t, J = 7.5 Hz, 3H). C NMR (125 MHz,
(CD ) SO) δ 166.2, 134.21, 134.19, 131.7, 131.5, 130.4, 129.6,
o
1
(3kc). White solid, m.p. 200-201 C, 37% yield (33.3mg). H
3
2
NMR (500 MHz, CDCl ) δ 10.80 (s, 1H), 8.85 (dd, J = 4.5, 1.5
128.4, 127.9, 127.8, 126.9, 126.6, 124.5, 124.2, 119.2.
3
Hz, 1H), 8.74 (d, J = 8.5 Hz, 1H), 8.42 (dd, J = 8.5, 1.5 Hz, 1H),