Methyl iodide → 3-Iodo-7-methyl-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

HRID 1037255노트

반응식

HRID 1037255 반응식
[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]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 866710193-iodo-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione

생성물 1

HCID 866710293-Iodo-7-methyl-2-phenyl-7H-pyrano[2,3-c]pyridine-4,8-dione수율 61.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  1. customthe reaction mixture was partitioned between ethyl acetate and water
  2. customThe resultant biphasic mixture was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic extracts were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue was crystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-7a10498b4aba47e18ba5ab0b5021d4b9
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546376B2

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