Potassium Carbonate → HCID 21460740, compound

HRID 1376098Notes

Reaction equation

HRID 1376098 reaction equation
F[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl.[NH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].CC(C)([O-])C.[K+]>ClCCl.CN1CCCC1=O>[NH2:5][C:4]1[C:3]2[C:2](=[CH:9][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:7][CH:6]=2)[NH:15][C:16]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5189732-Fluoro-4-(trifluoromethyl)benzonitrileHCID 2723640Glycine ethyl ester, hydrochlorideHCID 23665647Potassium tert-butoxide

Product 1

HCID 21460740HCID 21460740, compoundYield 23.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Under nitrogen, stir and heat a mixture of 2-fluoro-4-(trifluoromethyl)benzonitrile (1.0 g, 5.29 mmol), ethyl glycinate hydrochloride (886 mg, 6.3 mmol), potassium carbonate (1.46 g, 6.3 mmol) and 1-methyl-2-pyrrolidinone (20 mL) at 115–120° C. After six hours add potassium tert-butoxide (700 mg, 6.2 mmol), and stir at ambient temperature for 2 h. Quench into ice/water, extract the aqueous mixture with ether, wash the extract with water and dry it with magnesium sulfate. Filter and concentrate under vacuum to yield the crude product. Chromatograph the crude product on silica gel (10 g, Sepack cartridge) with dichloromethane as eluent to afford 332 mg (23%) of the title compound. Identical on TLC (silica gel, dichloromethane) to the compound disclosed in U.S. Pat. No. 5,189,054.

Workup

  1. temperatureheat
  2. stirringstir at ambient temperature for 2 h
  3. customQuench into ice/water
  4. extractionextract the aqueous mixture with ether
  5. washwash the
  6. extractionextract with water
  7. dry with materialdry it with magnesium sulfate
  8. filtrationFilter
  9. concentrationconcentrate under vacuum
  10. customto yield the crude product

Sources & evidence

ORD record
ord-d2e2e3c9a6014821a2434c10f1433769
Source dataset
uspto-grants-2007_01
Patent number
US07169925B2

Reaction notes

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