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

HRID 1622561Notes

Reaction equation

HRID 1622561 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:19]1[C:24](Br)=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[OH-].[Pd+2].[OH-].[Pd]>[C:1]([O:5][C:6](=[O:26])[NH:7][C@H:8]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1)[C:9]1[CH:14]=[CH:13][C:12]([C:15]([F:16])([F:17])[F:18])=[CH:11][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 71164782(S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate2×

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 (Intermediate 40, Step 5) (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 (1 atm) overnight. The mixture was next filtered through Celite® brand filter agent and the Celite® filter agent was 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 next filtered through Celite® brand
  2. filtrationfilter agent
  3. filtrationthe Celite® filter agent
  4. washwas washed with a solution of MeOH/EtOAc (1:1, 3×20 mL)
  5. concentrationThe combined filtrates were concentrated
  6. customdried

Sources & evidence

ORD record
ord-a697182366234f06943f389e33ed1ac3
Source dataset
uspto-grants-2014_07
Patent number
US08778941B2

Reaction notes

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