Methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate → Methyl 6-(2-fluoro-5-methoxyphenyl)-5-hydroxynicotinate

HRID 709797Notes

Reaction equation

HRID 709797 reaction equation
C([O:8][C:9]1[C:10]([C:19]2[CH:24]=[C:23]([O:25][CH3:26])[CH:22]=[CH:21][C:20]=2[F:27])=[N:11][CH:12]=[C:13]([CH:18]=1)[C:14]([O:16][CH3:17])=[O:15])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[F:27][C:20]1[CH:21]=[CH:22][C:23]([O:25][CH3:26])=[CH:24][C:19]=1[C:10]1[C:9]([OH:8])=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][N:11]=1

Participants

4

Reactant 1

HCID 117760070Methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate

Product 1

HCID 117759971Methyl 6-(2-fluoro-5-methoxyphenyl)-5-hydroxynicotinateYield 88.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under a nitrogen atmosphere, to a solution of methyl 5-(benzyloxy)-6-(2-fluoro-5-methoxyphenyl)nicotinate (1.50 g) in ethyl acetate (20 mL) was added 10% palladium-activated carbon (433 mg) and the mixture was stirred under a hydrogen atmosphere at room temperature for 20 hr. The reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure to give the title compound (1.00 g) as a yellow solid. This compound was used for the next step without further purification.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f2d064d607c440e494511cad9cd3d1be
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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