(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate → (S)-tert-butyl(pyridin-2-yl(4-(trifluoromethyl)phenyl)methyl)carbamate

HRID 509336Notes

Reaction equation

HRID 509336 reaction equation
Br[C:2]1[C:3]([C@@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1>CO.[OH-].[Pd+2].[OH-].[Pd]>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:2][C:3]=1[C@@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[C:9]1[CH:10]=[CH:11][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:13][CH:14]=1

Participants

5

Reactant 1

HCID 71164782(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

Product 1

HCID 71164819(S)-tert-butyl(pyridin-2-yl(4-(trifluoromethyl)phenyl)methyl)carbamate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of (S)-tert-butyl ((3-bromopyridin-2-yl)(4-(trifluoromethyl)-phenyl)methyl)carbamate (2.24 g, 5.19 mmol) in MeOH (20 mL) was added palladium hydroxide, (20 wt % Pd (dry basis) on carbon, wet, degussa type) (0.365 g, 2.60 mmol). The resulting mixture was then stirred at rt under H2 overnight. The mixture was filtered through Celite® brand filter agent and the solids were washed with a solution of MeOH/EtOAc (1:1, 3×20 mL). The combined filtrates were concentrated and dried to give the desired product as a yellow oil, which was used in the next step without further purification.

Workup

  1. filtrationThe mixture was filtered through Celite® brand
  2. filtrationfilter agent
  3. washthe solids were washed with a solution of MeOH/EtOAc (1:1, 3×20 mL)
  4. concentrationThe combined filtrates were concentrated
  5. customdried

Sources & evidence

ORD record
ord-5de529f82ada477f9d96e6b647035670
Source dataset
uspto-grants-2015_08
Patent number
US09096527B2

Reaction notes

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