The Journal of Organic Chemistry
Article
(m, 1H), 7.13 (d, J = 7.9 Hz, 1H), 2.64 (s, 3H); 13C{ H} NMR (126
1
4
-(Bis(phenylsulfonyl)methyl)-3-(pyridin-2-yl)benzonitrile (5c).
1
White solid (78.0 mg, 82% yield): mp 206−208 °C; H NMR (400
MHz, CDCl ) δ 8.53 (d, J = 4.1 Hz, 1H), 8.36 (d, J = 8.2 Hz, 1H),
MHz, CDCl ) δ 197.0, 156.2, 148.3, 144.6, 138.7, 137.6, 136.7, 134.2,
132.4, 130.4, 129.4, 129.2, 128.7, 124.5, 124.5, 122.9, 80.9, 26.7;
HRMS (ESI) m/z [M + H] Calcd for C H NO S 492.0934, found
3
3
+
7
3
1
1
1
.78 (dd, J = 8.2, 1.7 Hz, 1H), 7.72−7.64 (m, 6H), 7.64−7.56 (m,
2
6
22
5 2
H), 7.39 (t, J = 7.9 Hz, 4H), 7.33−7.27 (m, 1H), 7.00 (d, J = 7.8 Hz,
492.0930.
H); 13C{ H} NMR (101 MHz, CDCl ) δ 155.1, 148.4, 141.7, 138.7,
1
2-(2-(Bis(phenylsulfonyl)methyl)-4-chlorophenyl)pyridine (5k).
3
1
37.7, 134.4, 133.2, 132.8, 131.7, 129.1, 129.0, 128.8, 124.3, 123.1,
17.6, 114.3, 80.6; HRMS (ESI) m/z [M + H] Calcd for
White solid (79.1 mg, 82% yield): mp 230−232 °C; H NMR (500
+
MHz, CDCl ) δ 8.49 (d, J = 4.3 Hz, 1H), 8.12 (d, J = 2.0 Hz, 1H),
3
C H N O S 475.0781, found 475.0781.
7.74−7.66 (m, 5H), 7.62 (td, J = 7.8, 1.6 Hz, 1H), 7.56 (t, J = 7.5 Hz,
2H), 7.44 (dd, J = 8.4, 2.1 Hz, 1H), 7.38 (t, J = 7.8 Hz, 4H), 7.27−
25
19
2
4 2
2
-(2-(Bis(phenylsulfonyl)methyl)-4-methylphenyl)pyridine (5d).
1
13
1
White solid (82.4 mg, 89% yield): mp 192−194 °C; H NMR (500
7.20 (m, 2H), 6.96 (d, J = 7.9 Hz, 1H); C{ H} NMR (126 MHz,
MHz, CDCl ) δ 8.49 (d, J = 4.5 Hz, 1H), 7.90 (s, 1H), 7.76−7.65 (m,
CDCl ) δ 156.3, 148.2, 139.1, 138.8, 137.4, 134.8, 134.2, 131.7, 131.1,
3
3
5
H), 7.60 (t, J = 7.6 Hz, 1H), 7.55 (t, J = 7.4 Hz, 2H), 7.36 (t, J = 7.7
130.6, 129.2, 128.7, 125.7, 124.2, 122.5, 80.7; HRMS (ESI) m/z [M +
+
Hz, 4H), 7.31−7.25 (m, 1H), 7.25−7.21 (m, 1H), 7.21−7.16 (m,
H] Calcd for C H ClNO S 484.0439, found 484.0440.
2
4
19
4 2
1
3
1
1H), 6.99 (d, J = 7.8 Hz, 1H), 2.42 (s, 3H); C{ H} NMR (126
2-(2-(Bis(phenylsulfonyl)methyl)naphthalen-1-yl)pyridine (5l).
1
MHz, CDCl ) δ 157.3, 148.0, 139.2, 138.9, 138.0, 137.2, 133.9, 132.4,
White solid (88.0 mg, 88% yield): mp 203−205 °C; H NMR (500
3
1
(
31.3, 129.8, 129.2, 128.5, 124.1, 123.5, 121.9, 81.2, 21.3; HRMS
MHz, CDCl ) δ 8.64 (d, J = 3.9 Hz, 1H), 8.15 (d, J = 8.7 Hz, 1H),
3
ESI) m/z [M + H]+ Calcd for C H NO S 464.0985, found
7.96 (d, J = 8.7 Hz, 1H), 7.93−7.81 (m, 3H), 7.67 (t, J = 7.3 Hz, 1H),
7.62−7.49 (m, 5H), 7.43 (t, J = 7.4 Hz, 2H), 7.38−7.30 (m, 4H),
2
5
22
4 2
4
64.0983.
1
3
1
2
-(2-(Bis(phenylsulfonyl)methyl)-4-methoxyphenyl)pyridine (5e).
7.26−7.21 (m, 1H), 6.87 (d, J = 7.5 Hz, 1H), 5.94 (s, 1H); C{ H}
1
White solid (73.5 mg, 77% yield): mp 181−183 °C; H NMR (400
NMR (126 MHz, CDCl ) δ 155.4, 149.5, 141.4, 139.4, 138.5, 136.1,
3
MHz, CDCl ) δ 8.46 (d, J = 4.3 Hz, 1H), 7.87 (s, 1H), 7.75−7.66 (m,
134.2, 134.1, 131.6, 129.5, 129.4, 128.8, 128.8, 128.6, 128.2, 127.3,
3
5
1
1
1
1
H), 7.60−7.49 (m, 3H), 7.35 (t, J = 7.7 Hz, 4H), 7.23 (d, J = 8.6 Hz,
126.8, 126.8, 126.5, 126.2, 122.7, 121.4, 84.1; HRMS (ESI) m/z [M +
+
H), 7.18−7.11 (m, 1H), 7.04−6.96 (m, 1H), 6.90 (d, J = 7.9 Hz,
H] Calcd for C28
H22NO
S
4
2
500.0985, found 500.0985.
1
3
1
H), 3.88 (s, 3H); C{ H} NMR (101 MHz, CDCl ) δ 159.4, 157.1,
2-(3-(Bis(phenylsulfonyl)methyl)thiophen-2-yl)pyridine (5m).
3
1
47.9, 139.1, 137.1, 133.9, 133.3, 131.1, 129.1, 128.5, 125.0, 123.9,
21.7, 117.3, 116.1, 80.9, 55.5; HRMS (ESI) m/z [M + H] Calcd for
White solid (77.7 mg, 85% yield): mp 190−192 °C; H NMR (400
+
MHz, CDCl ) δ 8.45 (s, 1H), 8.37 (d, J = 4.2 Hz, 1H), 7.79−7.67 (m,
3
C H NO S 480.0934, found 480.0934.
5H), 7.55 (td, J = 7.8, 1.4 Hz, 1H), 7.48 (t, J = 7.4 Hz, 2H), 7.38−
25
22
5 2
13 1
3
-(Bis(phenylsulfonyl)methyl)-N,N-dimethyl-4-(pyridin-2-yl)-
7.29 (m, 5H), 7.18 (d, J = 8.0 Hz, 1H), 7.15−7.09 (m, 1H); C{ H}
1
aniline (5f). White solid (60.0 mg, 61% yield): mp 226−228 °C; H
NMR (101 MHz, CDCl ) δ 151.3, 148.2, 143.3, 138.9, 137.1, 134.0,
3
NMR (400 MHz, CDCl ) δ 8.44 (d, J = 4.4 Hz, 1H), 8.08 (s, 1H),
130.9, 128.9, 128.4, 125.0, 123.9, 122.5, 122.3, 79.6; HRMS (ESI) m/
3
+
7
1
1
.73 (d, J = 7.7 Hz, 4H), 7.53 (t, J = 7.4 Hz, 3H), 7.42 (d, J = 1.6 Hz,
z [M + H] Calcd for C H NO S 456.0392, found 456.0392.
2
2
18
4 3
H), 7.35 (t, J = 7.8 Hz, 4H), 7.22 (d, J = 8.7 Hz, 1H), 7.14−7.07 (m,
2-(3-(Bis(phenylsulfonyl)methyl)furan-2-yl)pyridine (5n). White
1
H), 6.98 (d, J = 7.0 Hz, 1H), 6.79 (d, J = 7.4 Hz, 1H), 3.03 (s, 6H);
solid (71.6 mg, 82% yield): mp 169−171 °C; H NMR (400 MHz,
1
3
1
C{ H} NMR (101 MHz, CDCl ) δ 157.8, 149.8, 147.7, 139.4,
CDCl ) δ 8.32 (d, J = 4.8 Hz, 1H), 8.17 (s, 1H), 7.87−7.78 (m, 4H),
3
3
1
1
36.9, 133.7, 130.7, 129.1, 128.4, 127.9, 124.3, 123.3, 120.8, 115.2,
13.6, 81.0, 40.1; HRMS (ESI) m/z [M + H] Calcd for
7.59 (td, J = 7.9, 1.7 Hz, 1H), 7.50−7.41 (m, 4H), 7.34 (t, J = 7.8 Hz,
+
13
1
4H), 7.12−7.06 (m, 1H), 6.99 (d, J = 1.8 Hz, 1H); C{ H} NMR
C H N O S 493.1250, found 493.1252.
(101 MHz, CDCl
) δ 151.6, 148.6, 148.2, 142.5, 138.6, 136.7, 134.1,
3
26
25
2
4 2
3
-(Bis(phenylsulfonyl)methyl)-4-(pyridin-2-yl)phenol (5g). White
129.0, 128.4, 122.6, 119.4, 113.4, 110.3, 78.3; HRMS (ESI) m/z [M +
1
+
solid (61.3 mg, 66% yield): mp 239−241 °C; H NMR (400 MHz,
H] Calcd for C22H18NO S 440.0621, found 440.0619.
5 2
DMSO-d ) δ 10.21 (s, 1H), 8.55 (d, J = 3.9 Hz, 1H), 8.12 (s, 1H),
2-(2-(Bis(phenylsulfonyl)methyl)-1H-pyrrol-1-yl)pyridine (5o).
6
1
7
7
1
1
1
.64 (t, J = 7.2 Hz, 3H), 7.59−7.49 (m, 5H), 7.49−7.42 (m, 4H),
White solid (10.5 mg, 12% yield): mp 155−157 °C; H NMR (500
.32−7.22 (m, 2H), 6.94 (d, J = 8.4 Hz, 1H), 6.86 (d, J = 7.9 Hz,
MHz, CDCl ) δ 8.25 (d, J = 4.2 Hz, 1H), 7.79−7.70 (m, 5H), 7.64 (t,
3
H); 13C{ H} NMR (101 MHz, DMSO-d ) δ 157.3, 156.4, 147.8,
1
J = 7.7 Hz, 1H), 7.53 (t, J = 7.1 Hz, 2H), 7.37 (t, J = 7.6 Hz, 4H),
6
1
3
38.8, 137.6, 134.4, 131.3, 131.3, 129.1, 128.1, 124.3, 123.7, 121.8,
18.0, 117.9, 79.9; HRMS (ESI) m/z [M + H] Calcd for
7.17−7.10 (m, 1H), 6.98−6.82 (m, 3H), 6.34−6.26 (m, 1H);
NMR (126 MHz, CDCl ) δ 151.5, 147.7, 139.0, 138.8, 134.0, 129.4,
128.5, 123.5, 121.4, 118.3, 116.5, 116.2, 110.9, 79.2; HRMS (ESI) m/
C
+
3
C H NO S 466.0777, found 466.0777.
24
20
5 2
+
3
-(Bis(phenylsulfonyl)methyl)-4-(pyridin-2-yl)aniline (5h). Light
z [M + H] Calcd for C22H N O S 439.0781, found 439.0777.
19 2 4 2
1
yellow solid (65.0 mg, 70% yield): mp 240−242 °C; H NMR (400
2-(Bis(phenylsulfonyl)methyl)-1-(pyridin-2-yl)-1H-indole (5p).
1
MHz, DMSO-d ) δ 8.49 (d, J = 4.2 Hz, 1H), 8.27 (s, 1H), 7.69−7.49
White solid (80.0 mg, 82% yield): mp 189−191 °C; H NMR (400
6
(
(
m, 7H), 7.44 (t, J = 7.7 Hz, 4H), 7.31 (d, J = 2.0 Hz, 1H), 7.22−7.14
m, 1H), 7.11 (d, J = 8.5 Hz, 1H), 6.82 (d, J = 8.0 Hz, 1H), 6.69 (dd,
MHz, CDCl ) δ 8.41 (d, J = 3.6 Hz, 1H), 7.82−7.71 (m, 5H), 7.70−
3
7.65 (m, 1H), 7.56 (t, J = 7.5 Hz, 2H), 7.38 (t, J = 7.8 Hz, 4H), 7.32−
7.27 (m, 1H), 7.26−7.19 (m, 4H), 7.14 (d, J = 8.0 Hz, 1H), 7.07 (s,
1
3
1
J = 8.4, 2.0 Hz, 1H), 5.79 (s, 2H); C{ H} NMR (126 MHz, DMSO-
d6) δ 157.1, 148.9, 147.5, 139.1, 137.4, 134.2, 130.8, 129.0, 128.0,
1
3
1
1H); C{ H} NMR (101 MHz, CDCl ) δ 149.8, 149.0, 138.8, 138.4,
3
1
27.3, 123.8, 123.1, 121.0, 116.0, 115.7, 79.9; HRMS (ESI) m/z [M +
136.7, 134.3, 129.5, 128.7, 127.5, 124.4, 122.9, 122.0, 121.9, 121.7,
+
+
H] Calcd for C H N O S 465.0937, found 465.0937.
120.2, 111.3, 110.7, 79.3; HRMS (ESI) m/z [M + H] Calcd for
24
21
2
4 2
2
-(2-(Bis(phenylsulfonyl)methyl)-4-nitrophenyl)pyridine (5i).
C
26
H
21
N
2
O
4
S
2
489.0937, found 489.0935.
1
White solid (91.8 mg, 93% yield): mp 269−271 °C; H NMR (400
6-(Bis(phenylsulfonyl)methyl)-2H-[1,2′-bipyridin]-2-one (5q).
1
MHz, DMSO-d ) δ 8.90 (d, J = 2.4 Hz, 1H), 8.68 (d, J = 4.8 Hz, 1H),
Light yellow solid (65.2 mg, 70% yield): mp184−186 °C; H NMR
(500 MHz, CDCl ) δ 8.44−8.35 (m, 1H), 7.83−7.66 (m, 7H), 7.58−
7.42 (m, 5H), 7.39−7.32 (m, 1H), 7.08 (d, J = 6.4 Hz, 1H), 7.01 (d, J
= 6.2 Hz, 1H), 6.73 (d, J = 8.3 Hz, 1H), 5.35 (s, 1H); C{ H} NMR
(126 MHz, CDCl ) δ 162.5, 149.7, 149.3, 138.8, 138.6, 137.9, 135.1,
132.2, 129.7, 129.1, 125.4, 124.4, 124.3, 111.2, 81.6; HRMS (ESI) m/
6
8
.43 (dd, J = 8.6, 2.4 Hz, 1H), 7.99 (s, 1H), 7.84−7.75 (m, 2H),
3
7.72−7.65 (m, 2H), 7.60−7.53 (m, 4H), 7.52−7.43 (m, 5H), 7.08 (d,
1
3
1
13
1
J = 7.9 Hz, 1H); C{ H} NMR (101 MHz, DMSO-d ) δ 154.0,
6
1
1
48.5, 146.7, 145.8, 138.3, 137.9, 135.0, 131.6, 129.4, 128.4, 125.8,
25.5, 125.2, 125.0, 123.9, 79.2; HRMS (ESI) m/z [M + H] Calcd
3
+
+
for C H N O S 495.0679, found 495.0679.
z [M + H] Calcd for C23H N O S 467.0730, found 467.0733.
19 2 5 2
24
19
2
6 2
1
-(3-(Bis(phenylsulfonyl)methyl)-4-(pyridin-2-yl)phenyl) Ethan-
2-(2-(Bis(phenylsulfonyl)methyl)cyclohex-1-en-1-yl)pyridine (5r).
1
1
1
-one (5j). White solid (84.4 mg, 86% yield): mp 228−230 °C; H
White solid (50.0 mg, 55% yield): mp 184−186 °C; H NMR (400
NMR (500 MHz, CDCl ) δ 8.60 (d, J = 1.2 Hz, 1H), 8.56 (d, J = 4.5
MHz, CDCl ) δ 8.40 (d, J = 4.1 Hz, 1H), 7.80 (d, J = 7.4 Hz, 4H),
3
3
Hz, 1H), 8.09 (d, J = 9.2 Hz, 1H), 7.74−7.68 (m, 6H), 7.58 (t, J = 7.4
Hz, 2H), 7.47 (d, J = 8.2 Hz, 1H), 7.40 (t, J = 7.8 Hz, 4H), 7.32−7.27
7.58 (t, J = 7.4 Hz, 2H), 7.45 (d, J = 15.6, 7.6 Hz, 5H), 7.14−7.06 (m,
1H), 7.00 (s, 1H), 6.70 (d, J = 7.8 Hz, 1H), 2.96−2.77 (m, 2H),
1
0185
J. Org. Chem. 2021, 86, 10177−10189