Stannous Chloride → 7-Amino-3-iodo-8-methoxy-2-phenyl-chromen-4-one

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-iodo-8-methoxy-7-nitro-2-phenyl-chromen-4-one (903 mg, 2.1 mmol) in ethyl acetate (7 mL) and IMS (7 mL) was added SnCl2 (2.37 g, 10.5 mmol). The reaction mixture was stirred at 80° C. for 1.5 hours before cooling to cool to RT. The resultant mixture was partitioned between ethyl acetate and water and the phases separated. The aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with brine, dried (NaSO4), filtered, and the solvent removed in vacuo. The resulting residue was subjected to flash chromatography (SiO2, gradient 40-50% ethyl acetate in cyclohexane) to give the title compound as a yellow solid (752 mg, 91%). LCMS (Method G): RT=3.35 min, [M+H]+=394.

Provenance & Evidence