[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([C:12]3([CH2:15][OH:16])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.[I:17]N1C(=O)CCC1=O.B(F)(F)F.O.O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>>[I:17][C:6]1[N:5]2[N:9]=[C:10]([C:12]3([CH2:15][OH:16])[CH2:14][CH2:13]3)[N:11]=[C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1A mixture of (1-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropyl)methanol (1.7 g, 7.76 mmol) and N-iodosuccinimide (1.7 g, 7.76 mmol) was treated with BF3.2H2O (8.5 g, 77.6 mmol, 5.3 ml) at RT. After 24 h, the reaction mixture was poured into a 1:1 mixture of the aq. solutions of NaHCO3 (1 M) and Na2S2O3 (1 M) and extracted with DCM. The combined organic phase was washed with H2O, over anhyd. Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by column chromatography to afford (1-(5-iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropyl)methanol (1.4 g, 52%) as a solid.
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