[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].C1COCC1.Br[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=1>CS(C)=O>[N:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[O:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=14-Hydroxybenzonitrile (1.00 g, 8.39 mmol) was dissolved in anhydrous DMSO (5.0 mL) and was slowly added a solution of potassium tert-butoxide in THF (1.0 M, 16.8 mmol). The solution was stirred for 2 hours 30 minutes. A solution of 2-bromopyridine (2.65 g, 16.8 mmol) in DMSO (5.0 mL) was then added to the reaction mixture the whole was heated at 160° C. for 115 hours. The cooled mixture was partitioned between ethyl acetate (100 mL) and water (100 mL). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×100 mL). The organic layers were dried with MgSO4, filtered and concentrated in vacuo. The crude solid was placed on a silica gel column and purified (EtOAc/Hex 1:6) to give the product as a light yellow solid (1.04 g, 63%). 1H NMR (500 MHz, CDCL3) δ(ppm): 7.01 (1H, d, J=8.2 Hz), 7.10 (1H, dd, J=7.2, 5.0 Hz), 7.24 (2H, d, J=9.0 Hz), 7.68 (2H, d, J=8.8 Hz), 7.77 (1H, ddd, J=8.3, 7.3, 2.0 Hz), 8.22 (1H, dd, J=5.0, 2.0 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 108.0, 112.8 (CH), 118.9, 120.0 (CH), 121.6 (CH), 134.1 (CH), 140.2 (CH), 147.9 (CH), 158.2, 162.5. MS (FAB+): 197 (MH+). HRMS for C12H8N2O (MH+): calculated: 197.0713; found 197.0715.
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