Br[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].N#N.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1>O.C(O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(C)C=CC=CC=1>[F:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:20][CH:19]=12-Bromo-3-hydroxypyridine (50 g, 0.29 mol), sodium carbonate (64 g, 0.60 mol), toluene (600 ml), and water (300 ml) were combined in a 2 liter 3-necked flask with condenser and N2 bubbler. A steady stream of N2 was passed over the reaction mixture while warming to 50° C. over 30 minutes. Tetrakis(triphenylphosphine) palladium(0) (10 g) was slurried in water then added to the reaction mixture then 4-fluorobenzeneboronic acid (46 g, 0.33 mol) was slurried in ethanol (100 ml) and added. The reaction mixture was refluxed for 5 hours then cooled and stirred at room temperature for 3 days. The organic layer was decanted off and concentrated in vacuo and the aqueous layer saturated with potassium carbonate and extracted with ethyl acetate (×4). The organics were combined and concentrated in vacuo then ethyl acetate (200 ml) added and the mixture heated. A yellow powder settled in the flask which was filtered off to give the title compound (25.1 g, 46%).
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