[F:1][C:2]1[C:7](I)=[CH:6][CH:5]=[CH:4][N:3]=1.[Li+].CC([N-][CH:14]([CH3:16])C)C.ClCCC[I:21].[CH2:22]([Cl:24])Cl>CCCCCCC.C1COCC1.C1COCC1>[Cl:24][CH2:22][CH2:14][CH2:16][C:7]1[C:2]([F:1])=[N:3][CH:4]=[CH:5][C:6]=1[I:21]To a −78° C. solution of 2-fluoro-3-iodopyridine (186 mg, 834 μmol) in tetrahydrofuran (4171 μl, 834 μmol) was added a solution of 2M LDA (500 μl, 1.00 mol) in heptane/THF at −78° C. After 1 h at −78° C., 1-chloro-3-iodopropane (512 mg, 2.50 mmol) in 0.5 mL of THF was added to the anion solution slowly at −78° C. After 30 min at −78° C., the reaction was warmed to rt and stirred overnight. The reaction was diluted with DCM, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by performing a column chromatography on silica gel using 95:05 Hex:EtOAc. Fractions containing the product were concentrated. 1H NMR showed product, 3-(3-chloropropyl)-2-fluoro-4-iodopyridine. Light yellow liquid/solid mixture was collected. MS Calcd for C8H8ClFIN: [M]+=299. Found: [M+H]+=300. HRMS Calcd for C8H8ClFIN: [M]+=298.9447. Found: [M+H]+=299.9752. mp=24-25° C.
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