4-[3-[(4-Methoxyphenyl)methoxy]-5-methylsulfonylphenyl]-6-methylfuro[2,3-c]pyridin-7-one → HCID 118022351, compound

HRID 575796Notes

Reaction equation

HRID 575796 reaction equation
COC1C=CC(C[O:10][C:11]2[CH:12]=[C:13]([C:21]3[C:22]4[CH:31]=[CH:30][O:29][C:23]=4[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=3)[CH:14]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:16]=2)=CC=1>CC(O)=O>[OH:10][C:11]1[CH:12]=[C:13]([C:21]2[C:22]3[CH:31]=[CH:30][O:29][C:23]=3[C:24](=[O:28])[N:25]([CH3:27])[CH:26]=2)[CH:14]=[C:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:16]=1

Participants

3

Reactant 1

HCID 1180218104-[3-[(4-Methoxyphenyl)methoxy]-5-methylsulfonylphenyl]-6-methylfuro[2,3-c]pyridin-7-one

Product 1

HCID 118022351HCID 118022351, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-[3-[(4-methoxyphenyl)methoxy]-5-methylsulfonylphenyl]-6-methylfuro[2,3-c]pyridin-7-one (370 mg, 0.84 mmol) in AcOH (6 mL) was heated to 100° C. for 12 h. After cooling to rt, the reaction mixture was evaporated to dryness in vacuo. The resulting residue was diluted with water and extracted with EtOAc (20 ml×3); the combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The resulting solid was suspensed in a 1:1 mixture of EtOAc and hexanes, sonicated for 1 min, and filtered. The filter cake was collected to afford the title compound (210 mg, 78%) as a gray solid. LCMS (M+H)+=320.

Workup

  1. customthe reaction mixture was evaporated to dryness in vacuo
  2. additionThe resulting residue was diluted with water
  3. extractionextracted with EtOAc (20 ml×3)
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. additionThe resulting solid was suspensed in a 1:1 mixture of EtOAc and hexanes
  9. customsonicated for 1 min
  10. filtrationfiltered
  11. customThe filter cake was collected

Sources & evidence

ORD record
ord-393f11911dfe444e90c9354735c3d9d1
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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