I[CH2:2][CH2:3][CH3:4].[I:5][C:6]1[N:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.C(=O)(O)[O-].[K+].CN(C=O)C>C(Cl)Cl.O>[I:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:2][CH2:3][CH3:4])=[CH:10][N:11]=1
Iodopropane (0.18 mL, 1.8 mmol) was added dropwise to a mixture comprising 6-iodopyridin-3-ol (0.32 g, 1.14 mmol), potassium bicarbonate (0.23 g, 1.7 mmol) and DMF (2 mL). The mixture was heated at 80° C. for 1 hour, cooled and diluted with methylene chloride and water. The aqueous layer was separated and extracted with methylene chloride (20 mL). The combined organic layers were washed with water 30 mL, dried (MgSO4) and concentrated under reduced pressure to provide 2-iodo-5-propoxypyridine. MS (ESI); Calculated for C8H10NIO, 266.1, Found (MH+): 222.
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