Potassium Carbonate → HCID 58338019, compound

HRID 2386918Notes

Reaction equation

HRID 2386918 reaction equation
F[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].[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+]>CS(C)=O>[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:3]=[N:4][CH:5]=[CH:6][C:7]=2[C:8]([F:11])([F:10])[F:9])=[CH:23][CH:22]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27828333-Fluoro-4-(trifluoromethyl)pyridineHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 58338019HCID 58338019, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-fluoro-4-trifluoromethylpyridine (1 g, 6.1 mmol) and [2-(4-hydroxyphenyl)-ethyl]-carbamic acid tert-butyl ester (1.44 g, 6.1 mmol) in DMSO (10 mL) was added K2CO3 (5 g, 36.2 mmol), and the mixture was heated at 100° C. for 30 min. After cooling, the solids were removed by suction filtration and washed with Et2O. The pooled filtrates were diluted with Et2O (75 mL) and washed with 0.01 N HCl. The organic layer was concentrated in vacuo. The residue was dissolved in Et2O/hexane and washed with 10% NaOH. The organic layer was filtered and vacuum dried to provide 1.4 g (60% yield) of {2-[4-(4-trifluoromethyl-pyridin-3-yloxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester as a clear, colorless oil.

Workup

  1. temperatureAfter cooling
  2. customthe solids were removed by suction filtration
  3. washwashed with Et2O
  4. additionThe pooled filtrates were diluted with Et2O (75 mL)
  5. washwashed with 0.01 N HCl
  6. concentrationThe organic layer was concentrated in vacuo
  7. dissolutionThe residue was dissolved in Et2O/hexane
  8. washwashed with 10% NaOH
  9. filtrationThe organic layer was filtered
  10. customvacuum dried

Sources & evidence

ORD record
ord-491efef53e9e4f9fbdefc87736d120aa
Source dataset
uspto-grants-2012_09
Patent number
US08268843B2

Reaction notes

Loading…