[F:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][N:3]=1.[CH:9]1(B(O)O)[CH2:11][CH2:10]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(C)C=CC=CC=1.O>C(Cl)(Cl)Cl.C(O)(C)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:9]1([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[N:3][CH:4]=2)[CH2:11][CH2:10]1
In a flask, combine 2-fluoro-5-iodo-pyridine (1.12 g, 5 mmol), cyclopropylboronic acid (645 mg, 7.5 mmol), palladium acetate (56 mg, 0.25 mmol), potassium phosphate (3.2 g, 15 mmol), and toluene-water (20:1, 21 mL). Heat the mixture at 100° C. for 4 hours. Dilute the mixture with chloroform-isopropanol (3:1, 100 mL). Wash the organic phase with saturated aqueous sodium chloride and water. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to a brown oil. Purify by column chromatography (20% ethyl acetate in hexane) to afford the title compound (430 mg, 63%) as a pale yellow oil. 1H NMR (400 MHz-CDCl3) δ 7.99 (d, J=3 Hz, 1H), 7.39 (td, J=3, 5 Hz, 1H), 6.79 (dd, J=3, 8 Hz, 1H), 0.96-1.02 (m, 2H), 0.63-0.69 (m, 2H).
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