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R. Karki et al. / Bioorg. Med. Chem. 18 (2010) 3066–3077
1H NMR (250 MHz, DMSO) d 12.31 (s, 2H, 2-phenyl 2-OH, 6-phe-
4.3.5. Synthesis of 3-(6-(furan-2-yl)-4-phenylpyridin-2-yl)-
phenol (19)
The procedure described in Section 4.3 was employed with
3b (0.33 g, 1.50 mmol), anhydrous ammonium acetate (1.15 g,
15.00 mmol), 5 (R3 = d) (0.47 g, 1.50 mmol), and glacial AcOH
(2 mL) to yield a white solid (0.41 g, 1.33 mmol).
nyl 20-OH), 8.20 (s, 2H, pyridine H-3, H-5), 7.98–7.95 (m, 4H, 2-phe-
nyl H-6, 6-phenyl H-6, 4-phenyl H-2, H-6), 7.60–7.52 (m, 3H, 4-
phenyl H-3, H-4, H-5), 7.32 (t, J = 8.2 Hz, 2H, 2-phenyl H-4, 6-phenyl
H-4), 6.99–6.93 (m, 4H, 2-phenyl H-3, H-5, 6-phenyl H-3, H-5).
13C NMR (62.5 MHz, DMSO) d 157.51, 155.59, 149.91, 137.76,
131.23, 129.77, 129.44, 128.95, 127.64, 122.26, 119.43, 117.90,
117.51.
Rf (ethyl acetate/n-hexane 1:3, v/v): 0.31; LC/MS/MS: retention
time: 7.77 min; [MH]+: 314.24.
1H NMR (250 MHz, CDCl3) d 7.88 (d, J = 1.3 Hz, 1H, pyridine H-3),
7.77(d, J = 1.3 Hz, 1H, pyridineH-5), 7.76–7.72(m, 2H, 4-phenylH-2,
H-6), 7.70 (t, J = 2.0 Hz, 1H, 2-phenyl H-2), 7.60 (d, J = 7.8 Hz, 1H, 2-
phenyl H-6), 7.55–7.47 (m, 4H, 4-phenyl H-3, H-4, H-5, 6-furan H-
5), 7.34 (t, J = 7.9 Hz, 1H, 2-phenyl H-5), 7.23 (d, J = 3.3 Hz, 1H, 6-fur-
an H-3), 6.91 (dd, J = 8.0, 2.5 Hz, 1H, 2-phenyl H-4), 6.56 (dd, J = 3.3,
1.7 Hz, 1H, 6-furan H-4), 6.12 (br, 1H, 2-phenyl 3-OH).
4.3.2. Synthesis of 3-(4,6-diphenylpyridin-2-yl)phenol (16)
The procedure described in Section 4.3 was employed with
3b (0.44 g, 2.00 mmol), anhydrous ammonium acetate (1.54 g,
20.00 mmol), 5 (R3 = a) (0.65 g, 2.00 mmol), and glacial AcOH
(2 mL) to yield a white solid (0.54 g, 1.67 mmol).
Rf (ethyl acetate/n-hexane 1:2, v/v): 0.44; LC/MS/MS: retention
time: 8.29 min; [MH]+: 324.27.
13C NMR (62.5 MHz, CDCl3) d 157.45, 156.27, 153.74, 150.08,
149.63, 143.29, 140.79, 138.48, 129.91, 129.12, 129.08, 127.08,
119.26, 117.29, 116.28, 115.33, 114.26, 112.13, 109.14.
1H NMR (250 MHz, CDCl3) d 8.18–8.15 (m, 2H, 6-phenyl H-2, H-
6), 7.88 (d, J = 1.1 Hz, 1H, pyridine H-5), 7.86 (d, J = 1.1 Hz, 1H, pyr-
idine H-3), 7.75–7.72 (m, 3H, 2-phenyl H-2, 4-phenyl H-2, H-6),
7.70 (d, J = 8.0 Hz, 1H, 2-phenyl H-6), 7.57–7.43 (m, 6H, 6-phenyl
H-3, H-4, H-5, 4-phenyl H-3, H-4, H-5), 7.36 (t, J = 8.0 Hz, 1H, 2-
phenyl H-5), 6.92 (dd, J = 8.0, 2.5 Hz, 1H, 2-phenyl H-4), 5.56 (br,
1H, 2-phenyl 3-OH).
4.3.6. Synthesis of 3-(4-phenyl-2,40-bipyridin-6-yl)phenol (22)
The procedure described in Section 4.3 was employed with
3b (0.44 g, 2.00 mmol), anhydrous ammonium acetate (1.54 g,
20.00 mmol), 5 (R3 = g) (0.65 g, 2.00 mmol), and glacial AcOH
(2 mL) to yield a white solid (0.42 g, 1.29 mmol).
13C NMR (62.5 MHz, CDCl3) d 157.56, 157.00, 156.05, 150.23,
141.08, 139.44, 138.85, 129.92, 129.11, 129.08, 129.03, 128.70,
127.16, 119.41, 117.49, 117.31, 116.13, 114.11.
Rf (ethyl acetate/n-hexane 1:1, v/v): 0.30; LC/MS/MS: retention
time: 6.90 min; [MH]+: 325.29.
1H NMR (250 MHz, DMSO) d 9.61 (br, 1H, 6-phenyl 3-OH), 8.76
(d, J = 4.3 Hz, 2H, 2-pyridine H-20, H-60), 8.33 (d, J = 1.1 Hz, 1H, pyr-
idine H-3), 8.29 (dd, J = 4.3, 1.4 Hz, 2H, 2-pyridine H-30, H-50), 8.21
(d, J = 1.1 Hz, 1H, pyridine H-5), 8.06–8.02 (m, 2H, 4-phenyl H-2, H-
6), 7.75 (s, 1H, 6-phenyl H-2), 7.72 (d, J = 8.4 Hz, 1H, 6-phenyl H-6),
7.61–7.51 (m, 3H, 4-phenyl H-3, H-4, H-5), 7.33 (t, J = 7.8 Hz, 1H, 6-
phenyl H-5), 6.91 (dd, J = 8.1, 1.7 Hz, 1H, 6-phenyl H-4).
13C NMR (62.5 MHz, DMSO) d 158.08, 157.15, 154.08, 150.59,
150.09, 145.95, 140.01, 137.56, 130.08, 129.77, 129.39, 127.70,
121.37, 118.40, 118.06, 117.69, 116.75, 114.00.
4.3.3. Synthesis of 3-(4-phenyl-6-(thiophen-2-yl)pyridin-2-yl)-
phenol (17)
The procedure described in Section 4.3 was employed with
3b (0.44 g, 2.00 mmol), anhydrous ammonium acetate (1.54 g,
20.00 mmol), 5 (R3 = b) (0.66 g, 2.00 mmol), and glacial AcOH
(2 mL) to yield a white solid (0.58 g, 1.76 mmol).
Rf (ethyl acetate/n-hexane 1:3, v/v): 0.34; LC/MS/MS: retention
time: 8.05 min; [MH]+: 330.24.
1H NMR (250 MHz, CDCl3) d 7.77 (s, 2H, pyridine H-3, H-5),
7.72–7.70 (m, 3H, 2-phenyl H-2, 4-phenyl H-2, H-6), 7.70 (d,
J = 4.4 Hz, 1H, 6-thiophene H-3), 7.68 (d, J = 8.4 Hz, 1H, 2-phenyl
H-6), 7.56–7.47 (m, 3H, 4-phenyl H-3, H-4, H-5), 7.42 (d,
J = 4.9 Hz, 1H, 6-thiophene H-5), 7.35 (t, J = 8.0 Hz, 1H, 2-phenyl
H-5), 7.15 (dd, J = 4.9, 3.7 Hz, 1H, 6-thiophene H-4), 6.93 (dd,
J = 8.0, 2.5 Hz, 1H, 2-phenyl H-4), 5.46 (br, 1H, 2-phenyl 3-OH).
13C NMR (62.5 MHz, CDCl3) d 156.79, 156.06, 152.66, 150.22,
145.16, 140.54, 138.62, 129.93, 129.11, 127.98, 127.73, 127.10,
124.73, 119.30, 117.03, 116.24, 115.60, 114.03.
4.3.7. Synthesis of 3,30-(4-phenylpyridine-2,6-diyl)diphenol (23)
The procedure described in Section 4.3 was employed with
3b (0.44 g, 2.00 mmol), anhydrous ammonium acetate (1.54 g,
20.00 mmol), 5 (R3 = i) (0.68 g, 2.00 mmol), and glacial AcOH
(2 mL) to yield a white solid (0.37 g, 1.16 mmol).
Rf (ethyl acetate/n-hexane 1:2, v/v): 0.35; LC/MS/MS: retention
time: 7.10 min; [MH]+: 340.27.
1H NMR (250 MHz, DMSO) d 9.57 (br, 2H, 2-phenyl 3-OH, 6-
phenyl 30-OH), 8.06 (s, 2H, pyridine H-3, H-5), 8.00–7.98 (m, 2H,
4-phenyl H-2, H-6), 7.73–7.68 (m, 4H, 2-phenyl H-2, H-6, 6-phenyl
H-2, H-6), 7.58–7.50 (m, 3H, 4-phenyl H-3, H-4, H-5), 7.32 (t,
J = 7.9 Hz, 2H, 2-phenyl H-5, 6-phenyl H-5), 6.89 (dd, J = 8.0,
1.7 Hz, 2H, 2-phenyl H-4, 6-phenyl H-4).
4.3.4. Synthesis of 3-(4-phenyl-6-(thiophen-3-yl)pyridin-2-yl)-
phenol (18)
The procedure described in Section 4.3 was employed with
3b (0.44 g, 2.00 mmol), anhydrous ammonium acetate (1.54 g,
20.00 mmol), 5 (R3 = c) (0.66 g, 2.00 mmol), and glacial AcOH
(2 mL) to yield a white solid (0.50 g, 1.53 mmol).
13C NMR (62.5 MHz, DMSO) d 158.01, 156.65, 149.62, 140.46,
138.02, 129.96, 129.51, 129.36, 127.56, 117.94, 116.79, 116.47,
113.96.
Rf (ethyl acetate/n-hexane 1:3, v/v): 0.34; LC/MS/MS: retention
time: 8.01 min; [MH]+: 330.24.
1H NMR (250 MHz, CDCl3) d 8.06 (dd, J = 3.0, 1.2 Hz, 1H, 6-thio-
phene H-2), 7.81 (dd, J = 5.5, 1.2 Hz, 1H, 6-thiophene H-4), 7.79 (d,
J = 1.3, 1H, pyridine H-3), 7.75 (d, J = 1.3 Hz, 1H, pyridine H-5),
7.73–7.69 (m, 3H, 2-phenyl H-2, 4-phenyl H-2, H-6), 7.67 (d,
J = 7.8 Hz, 1H, 2-phenyl H-6), 7.56–7.47 (m, 3H, 4-phenyl H-3, H-
4, H-5), 7.43 (dd, J = 5.0, 3.0 Hz, 1H, 6-thiophene H-5), 7.32 (t,
J = 8.0 Hz, 1H, 2-phenyl H-5), 6.93 (ddd, J = 8.0, 2.5, 0.7 Hz, 1H, 2-
phenyl H-4), 5.92 (br, 1H, 2-phenyl 3-OH)
4.3.8. Synthesis of 4-(4,6-diphenylpyridin-2-yl)phenol (24)
The procedure described in Section 4.3 was employed with
3c (0.56 g, 2.50 mmol), anhydrous ammonium acetate (1.92 g,
25.00 mmol), 5 (R3 = a) (0.81 g, 2.50 mmol), and glacial AcOH
(3 mL) to yield a white solid (0.41 g, 1.27 mmol).
Rf (ethyl acetate/n-hexane 1:2, v/v): 0.40; LC/MS/MS: retention
time: 8.03 min; [MH]+: 324.27.
1H NMR (250 MHz, CDCl3) d 8.19–8.17 (m, 2H, 6-phenyl H-2, H-
6), 8.12 (d, J = 8.6 Hz, 2H, 2-phenyl H-2, H-6), 7.83 (s, 1H, pyridine
H-5), 7.81 (s, 1H, pyridine H-3), 7.75–7.72 (m, 2H, 4-phenyl H-2, H-
6), 7.56–7.41 (m, 6H, 6-phenyl H-3, H-4, H-5, 4-phenyl H-3, H-4, H-
13C NMR (62.5 MHz, CDCl3) d 157.07, 156.16, 153.63, 150.19,
142.28, 140.96, 138.76, 129.88, 129.09, 129.02, 127.10, 126.46,
126.21, 123.91, 119.30, 117.18, 117.08, 116.16, 114.11.