5-(Benzyloxy)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine → 6-(2-Fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-ol

HRID 1049469Notes

Reaction equation

HRID 1049469 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[C:12]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:16]=2[F:23])=[N:13][CH:14]=1)C1C=CC=CC=1>C(OCC)(=O)C.[C].[Pd]>[F:23][C:16]1[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=1[C:12]1[N:13]=[CH:14][C:9]([OH:8])=[CH:10][C:11]=1[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26]

Participants

4

Reactant 1

HCID 1177596905-(Benzyloxy)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine

Product 1

HCID 1177596176-(2-Fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-olYield 100.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(benzyloxy)-2-(2-fluoro-5-methoxyphenyl)-3-neopentylpyridine (2.95 g) in ethyl acetate (50 mL) was added 10% palladium-carbon (628 mg) and, under a hydrogen atmosphere, the mixture was stirred at room temperature for 20 min. The catalyst was filtered and the filtrate was concentrated to give the title compound (2.26 g) as a white solid.

Workup

  1. filtrationThe catalyst was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-e10dac7f34b64a92b069fd814aecbd36
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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