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General Procedure for the Coupling of Halides with Amides: To a solution of MeONa (2.3 mmol) in DMSO (2 mL) were added CuI (29 mg, 0.15 mmol) and L1 (26 mg, 0.3 mmol). After stirring the mixture at r.t. for 30 min, the halide (1.5 mmol) and the amide (1.5 mmol) were added to the flask, and the reaction mixture was stirred at 120 °C for
24 h. The mixture was cooled to r.t., H2O (10 mL) was added, and the resulting suspension was extracted with EtOAc (4 × 10 mL). The extracted layer was dried over MgSO4, then concentrated, and purified by column chromatography on silica gel to provide the desired products.
22
3-(Pyridin-2-yl)quinazolin-4(3
H
)-one (3q): bright yellow solid; mp 135-137 °C(uncorrected). IR (KBr): 3448, 2924, 1688, 1610, 1590, 1563, 1478, 1440, 1294, 1255, 774, 760 cm-1. 1H NMR (400 MHz, CDCl3): δ = 8.65-8.66 (d, J = 4.4 Hz, 1 H), 8.57 (s, 1 H), 8.22-8.24 (d, J = 8.0 Hz, 1 H), 8.06-8.08 (t, J = 7.2 Hz, 1 H), 7.83-7.91 (m, 2 H), 7.74-7.76 (d,
J = 8.0 Hz, 1 H), 7.54-7.63 (m, 2 H). 13C NMR (100 MHz, CDCl3): δ = 160.1, 149.9, 149.6, 147.8, 146.1, 138.9, 135.4, 128.0, 127.8, 126.9, 124.6, 122.6, 122.1. LRMS (EI, 20 eV): m/z (%) = 223 (100) [M+]. Anal. Calcd for C13H9N3O: C, 69.95; H, 4.06; N, 18.82. Found: C, 69.46; H, 4.38; N, 18.65.
