Methyl iodide → 3-Iodo-7-methyl-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione
Reaction equation
[I:1][C:2]1[C:3](=[O:19])[C:4]2[CH:9]=[CH:8][NH:7][C:6](=[O:10])[C:5]=2[O:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[I:1][C:2]1[C:3](=[O:19])[C:4]2[CH:9]=[CH:8][N:7]([CH3:20])[C:6](=[O:10])[C:5]=2[O:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Participants
Procedure
To a mixture of 3-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione (50 mg, 0.137 mmol) and potassium carbonate (76 mg, 0.548 mmol) in DMF (2 mL) was added iodomethane (26 μL, 0.411 mmol) at RT. After 3 days, the reaction mixture was partitioned between ethyl acetate and water. The resultant biphasic mixture was separated, the aqueous layer was extracted with ethyl acetate and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resultant residue was crystallised from ethyl acetate to give the title compound (31.8 mg, 61%) as a cream solid. The mother liquors were evaporated, the residue was dissolved in DCM and subjected to flash chromatography (SiO2, gradient 70 to 100% ethyl acetate in cyclohexane) to afford a further quantity of the title compound (17.6 mg, 34%). LCMS (Method A): RT=3.78 min, [M+H]+=380.
Workup
- customthe reaction mixture was partitioned between ethyl acetate and water
- customThe resultant biphasic mixture was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washthe combined organic extracts were washed with water and brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe resultant residue was crystallised from ethyl acetate
Sources & evidence
- ORD record
- ord-7a10498b4aba47e18ba5ab0b5021d4b9
- Source dataset
- uspto-grants-2013_10
- Patent number
- US08546376B2
Reaction notes
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