Trifluoroacetic acid → 6-Fluoro-4-iodopyridin-3-amine
Reaction equation
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][C:11]([F:15])=[CH:12][C:13]=1[I:14])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:15][C:11]1[N:10]=[CH:9][C:8]([NH2:7])=[C:13]([I:14])[CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(6-Fluoro-4-iodopyridin-3-yl)-carbamic acid tert-butyl ester (1.75 g, 5.18 mmol) was dissolved in DCM (25 mL) and TFA (5 mL) added. The mixture was stirred at ambient temperature for 1 h and then evaporated in vacuo. The resultant residue was treated with saturated aqueous sodium hydrogen carbonate solution (25 mL), diluted with water (100 mL) and extracted into ethyl acetate (2×100 mL). The organic layer was separated, dried over sodium sulfate, filtered and evaporated in vacuo to afford the title compound as an orange oil, which crystallized on standing (1.23 g, 99%). 1H NMR (CDCl3, 300 MHz): 7.61 (d, J=1.6 Hz, 1H), 7.28-7.25 (m, 1H), 3.99 (s, 2H). LCMS (Method B): RT=2.52 min, M+H+=239.