5-Benzyloxy-2-difluoromethyl-1-ethyl-1H-pyridin-4-one → 2-Difluoromethyl-1-ethyl-5-hydroxy-1H-pyridin-4-one

HRID 912990Notes

Reaction equation

HRID 912990 reaction equation
C([O:8][C:9]1[C:10](=[O:20])[CH:11]=[C:12]([CH:17]([F:19])[F:18])[N:13]([CH2:15][CH3:16])[CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[F:19][CH:17]([F:18])[C:12]1[N:13]([CH2:15][CH3:16])[CH:14]=[C:9]([OH:8])[C:10](=[O:20])[CH:11]=1

Participants

5

Reactant 2

HCID 672829675-Benzyloxy-2-difluoromethyl-1-ethyl-1H-pyridin-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 250189052-Difluoromethyl-1-ethyl-5-hydroxy-1H-pyridin-4-oneYield 64.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 5-benzyloxy-2-difluoromethyl-1-ethyl-1H-pyridin-4-one (2.00 g, 7.16 mmol) and 10% Pd/C (200 mg) in methanol (75 mL) was hydrogenated under 15.0 psi pressure in a hydrogen atmosphere in a Parr apparatus for 23 min. The reaction mixture was worked up as described above. The title compound (0.87 g, 64%) was obtained as an off-white solid. HPLC purity (peak area percent) of the compound is 97.7% at λ=280 nm using HPLC Method 1 as described above. 1H NMR (400 MHz, DMSO-D6) δ (ppm): 7.61 (s, 1H), 7.15 (t, J=52.7 Hz, 1H, CF2H), 6.46 (s, 1H), 4.03 (q, J=7.0 Hz, 2H, N—CH2), 1.31 (t, J=7.1 Hz, 3H, CH3); MS-ESI (m/z): 190.2 [M+1]+, 142.2 (100%); Anal. Calcd. for C8H9F2NO2: C, 50.80; H, 4.80; N, 7.40%. Found: C, 50.64; H, 4.85; N, 7.38%.

Sources & evidence

ORD record
ord-95cfccd3b84d460999124412a2a35ee2
Source dataset
uspto-grants-2011_09
Patent number
US08026261B2

Reaction notes

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