Potassium Carbonate → {2-[4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

HRID 474742Notes

Reaction equation

HRID 474742 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=1.[C:12]([O:16][C:17](=[O:28])[NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=1)([CH3:15])([CH3:14])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:12]([O:16][C:17](=[O:28])[NH:18][CH2:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N:3]=2)=[CH:23][CH:22]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27364342-Bromo-5-(trifluoromethyl)pyridineHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 67775606{2-[4-(5-Trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

2-Bromo-5-(trifluoromethyl) pyridine (3000 mg, 13.274 mmol), [2-(4-hydroxy-phenyl)ethyl]-carbamic acid tert-butyl ester (3150 mg, 13.274 mmol) and potassium carbonate anhydrous (2752 mg, 19.911 mmol) were dissolved in DMF (150 ml) and reaction was stirred at 60° C. overnight. The reaction mixture was washed with EtOAc and water (3×). Organic layers were combined and dried over phase separator filter tube affording the crude product which was purified on Biotage SP-1 system using 50 g Si SNAP column. The column containing sample was eluted with EtOAc/CyHex gradient (0-30% of EtOAc/30 CV). Fractions with desired product were gathered and solvent was evaporated to give the required product {2-[4-(5-trifluoromethyl-pyridin-2-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester as a white solid (2200 mg, yield=42.9%, purity 99%). [M+H]+=383.39

Workup

  1. customreaction
  2. washThe reaction mixture was washed with EtOAc and water (3×)
  3. customdried over phase
  4. filtrationseparator filter tube
  5. customaffording the crude product which
  6. customwas purified on Biotage SP-1 system
  7. additionThe column containing sample
  8. washwas eluted with EtOAc/CyHex gradient (0-30% of EtOAc/30 CV)
  9. customsolvent was evaporated

Sources & evidence

ORD record
ord-fc7f624894964fb0a58bb44b8c52e7a3
Source dataset
uspto-grants-2014_01
Patent number
US08637536B2

Reaction notes

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