Acetic Acid → HCID 58608096, compound

HRID 2243568Notes

Reaction equation

HRID 2243568 reaction equation
[H][H].C([N:10]1[CH:15]=[CH:14][C:13](=[O:16])[C:12]2[C:17]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[C:18]([C:20]3[CH:25]=[CH:24][C:23]([O:26]CC4C=CC=CC=4)=[CH:22][CH:21]=3)[O:19][C:11]1=2)C1C=CC=CC=1.ClCCl.C(O)(=O)C>[Pd].C(OCC)(=O)C>[OH:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]2[O:19][C:11]3[NH:10][CH:15]=[CH:14][C:13](=[O:16])[C:12]=3[C:17]=2[C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 58608094HCID 58608094, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58608096HCID 58608096, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A 500-mL round bottom flask equipped with a rubber septum and hydrogen (g) balloon was charged with 7-benzyl-2-(4-benzyloxy-phenyl)-3-phenyl-7H-furo[2,3-b]pyridin-4-one (4a) (1.20 g, 2.50 mmol), dichloromethane (100 mL), acetic acid (100 mL), and ethyl acetate (20 mL). Palladium on carbon (10 wt %, 0.200 g) was added, and the system was evacuated and purged with hydrogen three times. The mixture stirred at room temperature for 24 h and was filtered through Celite. The filtrate was concentrated and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous phase was separated and extracted with ethyl acetate. The combined organic phases were washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, filtered and concentrated to afford 2-(4-hydroxy-phenyl)-3-phenyl-7H-furo[2,3-b]pyridin-4-one 5 as an off-white solid. MS (MH+) 304.1; Calculated 303 for C19H13NO3.

Workup

  1. customthe system was evacuated
  2. custompurged with hydrogen three times
  3. filtrationwas filtered through Celite
  4. concentrationThe filtrate was concentrated
  5. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  6. customThe aqueous phase was separated
  7. extractionextracted with ethyl acetate
  8. washThe combined organic phases were washed with saturated aqueous sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-78e524c8650a45f79e48cbff63a79117
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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