5-Benzyloxy-2-difluoromethyl-1H-pyridin-4-one → 2-(Difluoromethyl)-5-hydroxypyridin-4(1H)-one

HRID 913002Notes

Reaction equation

HRID 913002 reaction equation
C([O:8][C:9]1[C:10](=[O:18])[CH:11]=[C:12]([CH:15]([F:17])[F:16])[NH:13][CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[F:17][CH:15]([F:16])[C:12]1[NH:13][CH:14]=[C:9]([OH:8])[C:10](=[O:18])[CH:11]=1

Participants

4

Reactant 1

HCID 672821655-Benzyloxy-2-difluoromethyl-1H-pyridin-4-one

Product 1

HCID 672823252-(Difluoromethyl)-5-hydroxypyridin-4(1H)-oneYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5-Benzyloxy-2-difluoromethyl-1H-pyridin-4-one (300 mg, 1.19 mmol) was dissolved in methanol (20 mL) to give clear a yellow solution. Pd/C (55 mg) was added at RT. After purging with hydrogen gas, the mixture was hydrogenated at 50 psi H2 pressure for 15 min. The reaction mixture was filtered through a short pre-treated CELITE™ bed. The filtrate was collected, and the solvent was removed in vacuo to give the title compound as an off-white solid (170 mg, 88%) with an HPLC purity (peak percent area) of 98.8%. HPLC Method 1 is used (see Example 1). 1H NMR (300 MHz, DMSO-D6) δ (ppm): 10.3 (br s, 1H), 7.97 (s, 1H), 6.98 (s, 1H), 6.72 (t, J=55.4 Hz, 1H); MS (m/z) 162.2 [M+1]+, 142.1 (100%).

Workup

  1. customto give clear a yellow solution
  2. customAfter purging with hydrogen gas
  3. filtrationThe reaction mixture was filtered through
  4. additiona short pre-treated CELITE™ bed
  5. customThe filtrate was collected
  6. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4de343a052bb49cda23ae09b0eb7887a
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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