[F:1][C:2]1[C:7](I)=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[O:20]1[CH2:24][CH:23]=[CH:22][CH2:21]1>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[O:20]1[CH:21]=[CH:22][CH:23]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:24]1To a 500 mL round bottomed flask charged with 2-fluoro-3-iodopyridine (15.05 g, 67.5 mmol, Asymchem), tetrabutylammonium chloride (18.80 g, 67.6 mmol, Alfa Aesar), potassium carbonate (28.60 g, 207 mmol, Aldrich) and palladium(ii) acetate (1.48 g, 6.59 mmol, Strem) was added DMF (75 mL) followed by 2,5-dihydrofuran (50.00 mL, 678 mmol, Aldrich) and the reaction mixture was stirred vigorously at 25° C. for 2 h. The mixture was poured into 500 mL of water and the mixture was extracted with EtOAc (3×). The combined organic layers were evaporated onto silica gel and purified by flash chromatography (Isco (330 gram)) eluting with EtOAc:hexanes (0:1→1:2) to give a clear colorless oil. MS (ESI, pos. ion) m/z: 166.1 (M+1).
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