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

HRID 1037370Notes

Reaction equation

[I:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[C:6]([O:16][CH3:17])[C:7]([N+:13]([O-])=O)=[CH:8][CH:9]=2)[O:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Cl[Sn]Cl>C(OCC)(=O)C>[NH2:13][C:7]1[C:6]([O:16][CH3:17])=[C:5]2[C:10]([C:11](=[O:12])[C:2]([I:1])=[C:3]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[O:4]2)=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

temperaturebefore cooling
temperatureto cool to RT
customThe resultant mixture was partitioned between ethyl acetate and water
customthe phases separated
extractionThe aqueous layer was extracted with ethyl acetate
washthe combined organic extracts were washed with brine
dry with materialdried (NaSO4)
filtrationfiltered
customthe solvent removed in vacuo

Sources & evidence

ORD record: ord-6deb19dd29004bb4bf3de08ea5d9c326
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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