4-(benzyloxy)-1-(2-fluoro-4-(methylsulfonyl)phenyl)pyridin-2(1H)-one → 1-(2-fluoro-4-(methylsulfonyl)phenyl)-4-hydroxypyridin-2(1H)-one

HRID 1676180Notes

Reaction equation

HRID 1676180 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][C:16]=2[F:25])[C:11](=[O:26])[CH:10]=1)C1C=CC=CC=1>[Pd].C(Cl)Cl.CO.C1COCC1>[F:25][C:16]1[CH:17]=[C:18]([S:21]([CH3:24])(=[O:22])=[O:23])[CH:19]=[CH:20][C:15]=1[N:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]1=[O:26]

Participants

4

Reactant 1

HCID 673677574-(benzyloxy)-1-(2-fluoro-4-(methylsulfonyl)phenyl)pyridin-2(1H)-one

Product 1

HCID 673681541-(2-fluoro-4-(methylsulfonyl)phenyl)-4-hydroxypyridin-2(1H)-oneYield 107.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22912779methanol THF dichloromethaneSolvent2×

Procedure

To a 1 liter recovery flask added 10% palladium on carbon (1.75 g, 16.44 mmol), applied vacuum for 5 minutes then vented to nitrogen. Added 20 mL each of CH2Cl2/MeOH/THF to wet solid, then added a suspension of 4-(benzyloxy)-1-(2-fluoro-4-(methylsulfonyl)phenyl)pyridin-2(1H)-one (5.38 g, 14.41 mmol) in ˜80 mL each of CH2Cl2/MeOH/THF (total of 100 mL each solvent), all while keeping a nitrogen flow over mixture. Applied vacuum briefly then placed under an atmosphere of hydrogen for 105 minutes, filtered through a 60×60 mm pad of CELITE® 545 filter aid using an additional 200 mL each of MeOH and CH2Cl2, and concentrated the filtrate to give 4.4 g of crude product as an off-white powder. MS (ESI) 284.3 (M+1).

Workup

  1. customfor 5 minutes
  2. additionadded
  3. filtrationfiltered through a 60×60 mm pad of CELITE® 545
  4. filtrationfilter aid
  5. concentrationconcentrated the filtrate

Sources & evidence

ORD record
ord-ea9b2b15258c4cf5b13198938f056726
Source dataset
uspto-grants-2011_08
Patent number
US08003796B2

Reaction notes

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