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Organic & Biomolecular Chemistry
Page 5 of 6
DOI: 10.1039/C8OB00349A
Journal Name
ARTICLE
137.4, 136.2, 128.5, 128.2, 127.1, 127.0, 119.3, 115.7, 28.7, 28.6, 2,4-bis(4-bromophenyl)-6-methylpyridine (3l):
24.8, 15.6, 15.5; HRMS (ESI): m/z [M + Na]+ calcd for C22H23NNa:
324.1723; found: 324.1724.
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Yield 53% (53.4 mg); light yellow solid; mp 146–148 C; H NMR
(400 MHz, CDCl3): 7.91 (d, J = 8.4 Hz, 2H), 7.62 (d, J = 8.8 Hz, 4H),
7.59 (s, 1H), 7.53 (d, J = 8.4 Hz, 2H), 7.28 (s, 1H), 2.68 (s, 3H); 13C
NMR (100 MHz, CDCl3) δ (ppm) 159.2, 156.5, 148.5, 138.4, 137.5,
132.2, 131.8, 128.7, 128.6, 123.4, 119.8, 115.5, 24.8; HRMS (ESI):
m/z [M + H]+ calcd for C18H14Br2N: 401.9488; found: 401.9486.
2,4-bis(4-(tert-butyl)phenyl)-6-methylpyridine (3e):
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Yield 69% (61.6 mg); brown solid; mp 83–86 C; H NMR (400 MHz,
CDCl3): δ (ppm) 7.94 (d, J = 8.4 Hz, 2H), 7.70 (s, 1H), 7.62 (d, J = 8.0
Hz, 2H), 7.54–7.47 (m, 4H), 7.29 (s, 1H), 2.68 (s, 3H), 1.38 (s, 9H),
1.36 (s, 9H); 13C NMR (100 MHz, CDCl3) δ (ppm) 158.6, 157.6, 152.1, 2,4-bis(3,4-dichlorophenyl)-6-methylpyridine (3m):
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151.9, 149.2, 137.1, 135.9, 126.9, 126.7, 126.0, 125.6, 119.4, 115.8,
34.6(9), 34.6(5), 31.3(0), 31.2(9), 24.8; HRMS (ESI): m/z [M + H]+
calcd for C26H32N: 358.2529; found: 358.2527.
Yield 50% (47.9 mg); pink solid; mp 165–168 C; H NMR (400 MHz,
CDCl3): δ (ppm) 8.16 (d, J = 1.6 Hz, 1H), 7.88 (dd, J = 8.4, 2.0 Hz, 1H),
7.75 (d, J = 2.0 Hz, 1H), 7.61 (s, 1H), 7.60–7.52 (m, 2H), 7.49 (dd, J =
8.4, 2.0 Hz, 1H), 7.29 (s, 1H), 2.72 (s, 3H); 13C NMR (100 MHz, CDCl3)
δ (ppm) 159.5, 155.2, 147.5, 139.0, 138.3, 133.5, 133.4, 133.3,
133.0(5), 131.0(9), 130.7, 129.0, 128.9, 126.3, 126.2, 120.2, 115.5,
24.7; HRMS (ESI): m/z [M + H]+ calcd for C18H12Cl4N: 381.9718;
found: 381.9718.
2-methyl-4,6-diphenylpyridine (3f):
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Yield 84% (51.4 mg); pink solid; mp 68–70 C; H NMR (400 MHz,
CDCl3): δ (ppm) 8.03 (d, J = 7.2 Hz, 2H), 7.72 (s, 1H), 7.71–7.65 (m,
2H), 7.54–7.39 (m, 6H), 7.33 (s, 1H), 2.70 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ (ppm) 158.8, 157.7, 149.5, 139.8, 138.8, 129.0, 128.9,
128.8, 128.7, 127.1(4), 127.0(9), 119.8, 116.2, 24.8; HRMS (ESI): m/z 2-methyl-4,6-bis(4-(trifluoromethyl)phenyl)pyridine (3n):
[M + H]+ calcd for C18H16N: 246.1277; found: 246.1277.
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Yield 55% (52.4 mg); pink solid; mp 100–103 C; H NMR (400 MHz,
CDCl3): δ (ppm) 8.16 (d, J = 8.0 Hz, 2H), 7.77 (s, 4H), 7.74 (d, J = 6.8
Hz, 3H), 7.37 (s, 1H), 2.73 (s, 3H); 13C NMR (100 MHz, CDCl3) δ (ppm)
159.6, 156.3, 148.4, 142.7, 142.1, 131.2, 131.0, 130.9, 130.7, 127.5,
127.4, 126.1(3), 126.0(9), 126.0(5), 126.0, 125.8, 125.7(1), 125.6(8),
125.6, 125.5, 125.3, 122.8, 122.6, 120.7, 116.4, 24.8; HRMS (ESI):
m/z [M + H]+ calcd for C20H14F6N: 382.1025; found: 382.1029.
2,4-bis(4-methoxyphenyl)-6-methylpyridine (3g):
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Yield 69% (52.6 mg); yellow solid; mp 95–97 C; H NMR (400 MHz,
CDCl3): δ (ppm) 7.98 (d, J = 8.8 Hz, 2H), 7.64–7.58 (m, 3H), 7.21 (s,
1H), 6.99 (d, J = 8.8 Hz, 4H), 3.84 (s, 6H), 2.64 (s, 3H); 13C NMR (100
MHz, CDCl3) δ (ppm) 160.2(3), 160.2(1), 158.5, 157.1, 148.8, 132.5,
131.1, 128.3, 128.1, 118.6, 114.8, 114.3, 114.0, 55.2(9), 55.2(6),
24.7; HRMS (ESI): m/z [M + H]+ calcd for C20H20NO2: 306.1489; 2-methyl-4,6-bis(3-nitrophenyl)pyridine (3o):
Yield 46% (38.5 mg); white solid; mp 205–208 oC; 1H NMR (400 MHz,
found: 306.1492.
2,4-bis(4-ethoxyphenyl)-6-methylpyridine (3h):
CDCl3): δ (ppm) 8.94 (s, 1H), 8.55 (s, 1H), 8.44 (d, J = 7.6 Hz, 1H),
8.37–8.28 (m, 2H), 8.04 (d, J = 8.0 Hz, 1H), 7.82 (s, 1H), 7.78–7.66 (m,
2H), 7.45 (s, 1H), 2.76 (s, 3H); 13C NMR (100 MHz, CDCl3) δ (ppm)
160.1, 155.3, 148.9, 148.8, 147.6, 140.9, 140.1, 133.0, 132.9, 130.3,
129.8, 123.8(4), 123.7(8), 122.1(0), 122.0(5), 120.9, 115.9, 24.8;
HRMS (ESI): m/z [M + Na]+ calcd for C18H13N3NaO4: 358.0798; found:
358.0796.
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Yield 62% (51.6 mg); brown solid; mp 107–110 C; H NMR (400
MHz, CDCl3): δ (ppm) 7.97 (d, J = 8.8 Hz, 2H), 7.61 (d, J = 8.8 Hz, 3H),
7.22 (s, 1H), 7.02–6.96 (m, 4H), 4.08 (q, J = 6.8 Hz, 4H), 2.65 (s, 3H),
1.48–1.40 (m, 6H); 13C NMR (100 MHz, CDCl3) δ (ppm) 159.6(8),
159.6(5), 158.4, 157.2, 148.9, 132.3, 130.9, 128.3, 128.1, 118.5,
114.9, 114.8, 114.6, 63.6, 63.5, 24.7, 14.7(9), 14.7(7); HRMS (ESI):
m/z [M + H]+ calcd for C22H24NO2: 334.1802; found: 334.1806.
2-methyl-4,6-di(naphthalen-2-yl)pyridine (3p):
2,4-bis(benzo[d][1,3]dioxol-5-yl)-6-methylpyridine (3i):
Yield 47% (40.5 mg); white solid; mp 239–241 oC; 1H NMR (400 MHz,
CDCl3): δ (ppm) 8.55 (s, 1H), 8.22 (dd, J = 8.4, 1.6 Hz, 1H), 8.17 (s,
1H), 7.99–7.92 (m, 5H), 7.91–7.83 (m, 2H), 7.81 (dd, J = 8.8, 1.6 Hz,
1H), 7.58–7.48 (m, 4H), 7.45 (s, 1H), 2.76 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ (ppm) 159.0, 157.5, 149.4, 137.1, 136.1, 133.6, 133.5(2),
133.4(7), 133.4, 128.8, 128.7, 128.4(x 2), 127.7(1), 127.6(5), 126.7,
126.6, 126.4(4), 126.3(8), 126.3(7), 126.2, 124.9, 124.8, 120.0, 116.5,
24.9; HRMS (ESI): m/z [M + Na]+ calcd for C26H19NNa: 368.1410;
found: 368.1409.
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Yield 70% (58.3 mg); yellow solid; mp 145–148 C; H NMR (400
MHz, CDCl3): δ (ppm) 7.56–7.50 (m, 3H), 7.21–7.12 (m, 3H), 6.93–
6.87 (m, 2H), 6.02 (s, 2H), 6.00 (s, 2H), 2.64 (s, 3H); 13C NMR (100
MHz, CDCl3) δ (ppm) 158.6, 157.0, 149.0, 148.4, 148.3(0), 148.2(6),
148.1, 134.3, 132.9, 121.0, 120.9, 119.0, 115.1, 108.7, 108.4, 107.6,
107.3, 101.4, 101.2, 24.74; HRMS (ESI): m/z [M + H]+ calcd for
C20H16NO4: 334.1074; found: 334.1073.
2,4-bis(4-fluorophenyl)-6-methylpyridine (3j):
2-methyl-4,6-di(thiophen-2-yl)pyridine (3q):
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Yield 58% (40.7 mg); pink solid; mp 95–98 C; H NMR (400 MHz,
CDCl3): δ (ppm) 8.06–7.96 (m, 2H), 7.68–7.59 (m, 3H), 7.26 (s, 1H),
7.17 (q, J = 8.8 Hz, 4H), 2.67 (s, 3H); 13C NMR (100 MHz, CDCl3) δ
(ppm) 164.7, 164.6, 162.2, 162.1, 159.0, 156.6, 148.6, 135.8, 134.8,
128.9, 128.8(4), 128.7(6) 119.6, 116.1, 115.9, 115.7, 115.6, 115.5,
24.8; HRMS (ESI): m/z [M + H]+ calcd for C18H14F2N: 282.1089; found:
282.1088.
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Yield 82% (52.7 mg); brown oil; H NMR (400 MHz, CDCl3): δ (ppm)
7.68–7.60 (m, 2H), 7.52 (dd, J = 4.0, 1.2 Hz, 1H), 7.44–7.36 (m, 2H),
7.21 (s, 1H), 7.17–7.08 (m, 2H), 2.60 (s, 3H); 13C NMR (100 MHz,
CDCl3) δ (ppm) 159.0, 152.6, 144.8, 142.3, 141.5, 128.3, 127.9,
127.4, 126.9, 125.2, 124.6, 117.9, 112.5, 24.5; HRMS (ESI): m/z [M +
H]+ calcd for C14H12NS2: 258.0406; found: 258.0408.
2-methyl-4,6-di(thiophen-3-yl)pyridine (3r):
2,4-bis(4-chlorophenyl)-6-methylpyridine (3k):
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Yield 61% (47.7 mg); white solid; mp 130–133 oC; 1H NMR (400 MHz,
CDCl3): δ (ppm) 7.97 (d, J = 8.4 Hz, 2H), 7.63 (s, 1H), 7.59 (d, J = 8.4
Hz, 2H), 7.45 (t, J = 8.4 Hz, 4H), 7.28 (s, 1H), 2.68 (s, 3H); 13C NMR
(100 MHz, CDCl3) δ (ppm) 159.2, 156.5, 148.4, 138.0, 137.1, 135.2,
135.0, 129.3, 128.9, 128.4, 128.3, 119.8, 115.6, 24.8; HRMS (ESI):
m/z [M + H]+ calcd for C18H14Cl2N: 314.0498; found: 314.0495.
Yield 66% (42.4 mg); yellow solid; mp 68–71 C; H NMR (400 MHz,
CDCl3): δ (ppm) 7.95 (d, J = 2.0 Hz, 1H), 7.71–7.65 (m, 2H), 7.60 (s,
1H), 7.49–7.43 (m, 2H), 7.40 (dd, J = 4.8, 2.8 Hz, 1H), 7.25 (s, 1H),
2.64 (s, 3H); 13C NMR (100 MHz, CDCl3) δ (ppm) 158.9, 153.6, 143.8,
142.3, 140.0, 126.9, 126.4, 126.2, 125.9, 123.7, 122.8, 118.7, 115.0,
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