Synthesis of (aryl/heteroaryl)-(6-(aryl/heteroaryl)pyridin-3-yl)methanones
precipitate was filtered and washed (cold i-PrOH). The combined solvent was
evaporated and the crude residue was subjected to column chromatography (silica
gel, hexane–EtOAc, 6:4) to give 2-(5-fluoro-2-methyl-2,3-dihydrobenzofuran-7-yl)-
6
-methyl pyridine 2d white solid (0.38 g, 78 %),
p-Tolyl(6-p-tolylpyridin-3-yl)methanone (2a)
1
H NMR (300 MHz, CDCl ) d 8.98 (d, J = 1.5 Hz, 1H), 8.14 (dd, J = 2.2 Hz,
3
J = 6.0 Hz, 1H), 7.97 (d, J = 8.3 Hz, 2H), 7.81 (d, J = 8.3 Hz, 1H), 7.74 (d,
1
3
J = 8.3 Hz, 2H), 7.28 (q, J = 6.0 Hz, 4H), 2.46 (s, 3H), 2.43 (s, 3H). C NMR
(
75 MHz, CDCl ) d 194.2, 160.1, 151.0, 143.8, 140.1, 138.0, 134.4, 131.2, 130.1,
3
1
1
29.6, 129.2, 127.2, 119.5, 21.6, 21.3. IR (KBr) 2925, 1692, 1580, 1473, 1390,
-
325, 1225, 1175, 1031, 789 cm . MS (ESI) m/z 288 [M?H] .
1
?
Furan-2-yl(6-(furan-2-yl)pyridin-3-yl)methanone (2b)
1
H NMR (300 MHz, CDCl ) d 9.21 (d, J = 1.5 Hz, 1H), 8.34 (dd, J = 2.66 Hz,
3
J = 6.04 Hz, 1H), 7.79 (d, J = 9.06 Hz, 1H), 7.70 (s, 1H),7.53 (s,1H), 7.34 (d,
J = 3.02 Hz, 1H), 7.22 (d, J = 3.77 Hz, 1H), 6.63 (dd, J = 3.77 Hz, J = 1.51 Hz,
1
3
1
1
1
H), 6.57 (dd, J = 1.51 Hz, J = 2.26 Hz, 1H). C NMR (75 MHz, CDCl ) d
3
79.7, 150.6, 147.2, 144.5, 137.6, 120.4, 117.8, 112.5, 111.2. IR (KBr) 2923, 2853,
-
639, 1590, 1390, 1307, 1190, 1080, 953, 882, 767 cm MS (ESI) m/z 240
1
?
[
M?H] .
(
(
4-Fluoro-2-methoxyphenyl)(6-(4-fluoro-2-methoxyphenyl)pyridin-3-yl)methanone
2c)
1
H NMR (300 MHz, CDCl ) d 8.90 (s, 1H), 8.13 (dd, J = 2.26 Hz, J = 6.05 Hz,
3
1
J = 7.55 Hz, 2H), 7.02–7.08 (m, 1H), 6.89–6.95 (m, 2H), 3.87 (s, 3H), 3.72 (s, 3H).
H), 8.05 (d, J = 8.30 Hz, 1H), 7.72 (dd, J = 3.02 Hz, J = 6.04 Hz, 1H), 7.16 (d,
1
3
C NMR (75 MHz, CDCl ) d 197.5, 158.8, 158.4, 155.7, 153.6, 153.4, 151.0,
3
1
5
7
3
36.4, 124.5, 118.9, 118.6, 118.1, 117.8, 117.1, 116.8, 116.4, 112.6, 112.5, 56.14,
6.10. IR (KBr) 2926, 2852, 1657, 1588, 1495, 1369, 1260, 1176, 1025, 854, 806,
-
1
?
31 cm . MS (ESI) m/z 356 [M?H] ; HR-MS (ESI) Calcd for C H NO F
3 2
2
0
16
56.1098; found: 356.1099.
(2,4-Dimethyl-2,3-dihydro-benzofuran-7-yl)-[6-(2,4-dimethyl-2,3-dihydro-
benzofuran-7-yl)-pyridin-3-yl]-methanone (2d)
1
H NMR (400 MHz, CDCl ) d 8.92 (s, 1H), 8.20 (d, J = 8.30 Hz, 1H), 8.09 (d,
3
J = 8.30 Hz, 1H), 8.00 (d, J = 7.55 Hz, 1H), 7.34 (d, J = 8.30 Hz, 1H), 6.74 (d,
J = 7.55 Hz, 1H), 6.70 (d, J = 7.55 Hz, 1H), 5.01–5.08 (m, 1H), 4.90–4.97 (m,
1
H), 3.21–3.30 (m, 2H), 2.68–2.78 (m, 2H), 2.27(s, 3H), 2.25(s, 3H), 1.54 (d,
1
3
J = 6.04 Hz, 3H), 1.41(d, J = 6.04 Hz, 3H). C NMR (75 MHz, CDCl ) d 192.4,
3
1
58.3, 157.6, 157.5, 150.8, 139.5, 137.3, 136.4, 131.0, 129.6, 128.4, 128.2, 127.4,
22.5, 122.3, 122.0, 121.3, 118.2, 80.4, 79.8, 35.7, 35.4, 22.1, 21.9, 19.3, 19.0. IR
1
123