HCID 67072314, compound → HCID 67072607, compound

HRID 1895679Notes

Reaction equation

HRID 1895679 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)[C:11](=[O:25])[CH:10]=1)C1C=CC=CC=1>[Pd].C1COCC1.CO>[OH:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:19][CH:20]=2)[C:11](=[O:25])[CH:10]=1

Participants

5

Reactant 1

HCID 67072314HCID 67072314, compound

Product 1

HCID 67072607HCID 67072607, compoundYield 101.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirring suspension of 4-(benzyloxy)-1-(4-(methylsulfonyl)phenyl)pyridin-2(1H)-one (3.0 g, 8.44 mmol) and palladium on activated carbon (1.63 g, 10 wt. %, wet, Aldrich) in THF (150 mL) and methanol (250 mL) was placed under hydrogen (balloon) for 1 h. The resulting mixture was purged with nitrogen and then diluted with THF (150 mL) and methanol (50 mL). After stirring under nitrogen for 30 min, the mixture was filtered through a pad of CELITE® 545 filter aid and the filtrate was evaporated under reduced pressure to give 2.28 g crude product as a dark greenish solid. MS (ESI) 266 (M+H).

Workup

  1. customThe resulting mixture was purged with nitrogen
  2. additiondiluted with THF (150 mL) and methanol (50 mL)
  3. filtrationthe mixture was filtered through a pad of CELITE® 545
  4. filtrationfilter aid
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ba6c0f552490410ea51ef98d395ab87e
Source dataset
uspto-grants-2013_08
Patent number
US08513424B2

Reaction notes

Loading…