Iodine chloride → HCID 71150603, compound

Participants

Reaction Steps

Methyl 4-amino-5-fluoro-3-methoxy-6-(4-(trimethylsilyl)phenyl)picolinate (239 mg, 0.686 mmol) was dissolved in 1,2-dichloroethane (3.4 mL) and iodine monochloride (78 μL, 1.557 mmol). The reaction mixture was stirred at room temperature for 48 h. The mixture was quenched with 10% Na2S2O3 (2 mL) and stirred at room temperature for 1 h. The mixture was extracted with CH2Cl2 (3×5 mL), and the combined organic extracts were dried over Na2SO4 and concentrated in vacuo. The product was purified via RP-HPLC (CH3CN/H2O) to yield the title compound as an orange solid (270 mg, 98%): 1H NMR (400 MHz, DMSO-d6) δ 7.86 (d, J=8.5 Hz, 2H), 7.65-7.53 (m, 2H), 6.54 (s, 2H), 3.86 (s, 3H), 3.77 (s, 3H); 19F NMR (376 MHz, DMSO-d6) δ −140.64; ESIMS m/z 403.61 ([M+H]+).

Provenance & Evidence