Potassium Carbonate → HCID 11429549, compound

HRID 2358299Notes

Reaction equation

HRID 2358299 reaction equation
[CH:1]1([N:4]2[C:13]([C:14]#[N:15])=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([OH:23])[CH:10]=3)[C:5]2=[O:24])[CH2:3][CH2:2]1.C([O-])([O-])=O.[K+].[K+].O([CH2:39][C:40]([F:43])([F:42])[F:41])S(C(F)(F)F)(=O)=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH:1]1([N:4]2[C:13]([C:14]#[N:15])=[C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=3)[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([O:23][CH2:39][C:40]([F:43])([F:42])[F:41])[CH:10]=3)[C:5]2=[O:24])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 516892Sodium BicarbonateHCID 11393032HCID 11393032, compound

Product 1

HCID 11429549HCID 11429549, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of the phenol 62 (64 mg, 0.2 mmol), K2CO3 (83 mg, 0.6 mmol) and trifluoroethyl triflate (70 mg, 0.3 mmol) in DMF (3 mL) was heated at 50° C. for 30 min. The reaction was cooled, poured into saturated aqueous NaHCO3 and extracted with EtOAc. The combined organic extracts were washed once with 1N HCl and brine, dried with Na2SO4, filtered and concentrated in vacuo. Trituration of the residue with EtOAc/Hexane provided desired product 63.

Workup

  1. temperatureThe reaction was cooled
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed once with 1N HCl and brine
  4. dry with materialdried with Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fcb69742af384b33840631072b12e7c1
Source dataset
uspto-grants-2010_07
Patent number
US07763614B2

Reaction notes

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