4'-(4-METHOXYPHENYL)-2,2':6',2''-TERPYRIDINE

General procedure: Synthesis of 4′-(3-methoxyphenyl)-2, 2′:6′, 2″-terpyridine (3-MeO-Phtpy), 4′-(2-methoxyphenyl)-2, 2′:6′, 2″-terpyridine (2-MeO-Phtpy) and 4′-(4-methoxyphenyl)-2, 2′:6′, 2″-terpyridine (4-MeO-Phtpy) were performed using the methods described previously [27–33]. 2-Acetylpyridine (2.813g, 23.2mmol, 2 eq.) was added to 2-methoxybenzaldehyde, 3-methoxybenzaldehyde or 4-methoxybenzaldehyde (11.6mmol, 1 eq.) dissolved in 50mL ethanol. KOH pellets (46.5mmol, 4 eq.) were added to this solution. The reaction mixture was stirred at room temperature for 10min. NHGeneral procedure: Ketone (20 mmol) (2-acetylpyridine, 2-acetylthiazole or 2-acetylpyrazine)was added to a solution of aldehyde (10 mmol) (4-methoxybenzaldehyde, 4-methoxy-1-naphthaldehyde or 6-methoxy-2-naphthaldehyde) in EtOH (75 mL). KOH (1.54 g, 27.5 mmol) and NH3(aq)(35 mL) were then added. The solution was stirred at room temp. for 24 h. The solid was collected by filtration and washed with H2O. Recrystallization from ethanol (L1, L4, L7) or toluene (L2, L3, L5, L6, L8, L9) afforded a crystalline solid. 4′-(4-methoxy-1-phenyl)-2, 2′:6′, 2″-terpyridine (L1): Yield: 37percent. IR(KBr, cm−1): 1588(s), 1467(m), 1389(m), 1204(m), 1157(m), 1069(m), 790(m), 739(m) and 655(m). NMR: 1H NMR (400 MHz, CDCl3) δ 8.73 (d, J=4.1 Hz, 2H, HA1), 8.71 (s, 2H, HB2), 8.67 (d, J=7.9 Hz, 2H, HA4), 7.90–7.85 (m, 4H, HC2+A3), 7.37–7.33 (m, 2H, HA2), 7.03 (d, J=8.7 Hz, 2H, HC3), 3.88 (s, 3H, HC5). 13C NMR(100 MHz, CDCl3) δ 160.66, 156.55, 155.99, 149.90, 149.24, 136.96, 130.92, 128.67, 123.87, 121.49, 118.42, 114.46, 55.52. C22H17N3O(339.39 g mol−1): calcd C, 77.86; H, 5.05; N, 12.38percent; found: C, 77.46;H, 5.35; N, 12.25percent. DSC: (I run) Tm=164 °C; (II run) Tg=30, Tc=82and Tm=163 °C.

Molecular Weight:339.4
XLogP3:3.7
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:339.137162174
Monoisotopic Mass:339.137162174
Topological Polar Surface Area:47.9
Heavy Atom Count:26
Complexity:398
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes