Potassium tert-butoxide → HCID 69671072, compound

HRID 1191641Notes

Reaction equation

HRID 1191641 reaction equation
[CH3:1]C(C)([O-])C.[K+].[C:7]1([C:13]#[C:14][NH:15][C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:18][CH:17]=2)[CH:12]=[CH:11][CH:10]=[CH:9]C=1>CN1CCCC1=O.O>[C:13]1([C:14]2[NH:15][C:16]3[C:17]([CH:1]=2)=[CH:18][C:19]([O:22][C:23]([F:24])([F:25])[F:26])=[CH:20][CH:21]=3)[CH:9]=[CH:10][CH:11]=[CH:12][CH:7]=1

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 69670919HCID 69670919, compound

Product 1

HCID 69671072HCID 69671072, compoundYield 83.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Procedure

To a solution of potassium tert-butoxide (173 mg) in 1-methyl-2-pyrrolidone (3.7 mL) was added dropwise a solution of 2-phenylethynyl-4-trifluoromethoxyaniline (204 mg) in 1-methyl-2-pyrrolidone (3.7 mL) at room temperature under stirring, and the mixture was stirred for 6 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (171 mg).

Workup

  1. stirringthe mixture was stirred for 6 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-fba0c553f96a4ecf8a14cab7cc9516d8
Source dataset
uspto-grants-2014_03
Patent number
US08680120B2

Reaction notes

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