3-(Benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridine → 5-(((Tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridin-3-ol

HRID 709779Notes

Reaction equation

HRID 709779 reaction equation
C([O:8][C:9]1[C:10]([C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2[F:32])=[N:11][CH:12]=[C:13]([CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH:14]=1)C1C=CC=CC=1>[Pd].C(OCC)(=O)C>[Si:17]([O:16][CH2:15][C:13]1[CH:14]=[C:9]([OH:8])[C:10]([C:24]2[CH:29]=[C:28]([O:30][CH3:31])[CH:27]=[CH:26][C:25]=2[F:32])=[N:11][CH:12]=1)([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18]

Participants

4

Reactant 1

HCID 1317339163-(Benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridine

Product 1

HCID 1317339175-(((Tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridin-3-olYield 103.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Under a hydrogen atmosphere, a mixture of 3-(benzyloxy)-5-(((tert-butyldimethylsilyl)oxy)methyl)-2-(2-fluoro-5-methoxyphenyl)pyridine (2.81 g), 10% palladium-activated carbon (280 mg) and ethyl acetate (30 mL) was stirred at room temperature for 30 min. The catalyst was filtered off, and the solvent in the filtrate was evaporated under reduced pressure to give the title compound (2.33 g) as a pale-yellow solid.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent in the filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-2ca4c48aca034a86b36c936bb8ad4614
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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