Chlorodifluoromethane → 8-Difluoromethoxy-3-iodo-2-phenyl-pyrano[2,3-c]pyridin-4-one

HRID 1037232Notes

Reaction equation

Cl[CH:2]([F:4])[F:3].[I:5][C:6]1[C:7](=[O:23])[C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[C:9]=2[O:15][C:16]=1[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:3][CH:2]([F:4])[O:14][C:10]1[N:11]=[CH:12][CH:13]=[C:8]2[C:7](=[O:23])[C:6]([I:5])=[C:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[O:15][C:9]=12

Participants

Conditions

Temperature: 40 °C

Procedure

Chlorodifluoromethane was bubbled into a solution of 3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione (100 mg, 0.27 mmol) and potassium carbonate (55 mg, 0.40 mmol) in DMF (3.0 mL) over 2 min. The reaction mixture was stirred at 40° C., for 2 days under a chlorodifluoromethane balloon. The resulting mixture was partitioned between ethyl acetate (40 mL) and water (20 mL) and the phases were separated. The organic layer was washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. The resulting residue was subjected to flash chromatography (SiO2, 20% ethyl acetate in cyclohexane) to give the title compound as a white solid (33 mg, 29%). LCMS (Method B): RT=4.46 min, [M+H]+=416.

Workup

customThe resulting mixture was partitioned between ethyl acetate (40 mL) and water (20 mL)
customthe phases were separated
washThe organic layer was washed with brine (20 mL)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d470e7c92d034b3e9b5d3655fc3909c3
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546376B2

Reaction notes

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