HCID 58136639, compound → HCID 58136339, compound

HRID 1476064Notes

Reaction equation

HRID 1476064 reaction equation
[NH2:1][C:2]1[C:3]([F:17])=[C:4](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:5]=[CH:6][CH:7]=1>[Pd].C(O)C.C1COCC1>[NH2:1][C:2]1[C:3]([F:17])=[C:4]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 1

HCID 58136639HCID 58136639, compound

Product 1

HCID 58136339HCID 58136339, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Palladium on carbon (10%) was added to a solution of 1660 mg (7.0 mmol) of tert-butyl (2E)-3-(3-amino-2-fluorophenyl)acrylate in a mixture of 5 ml of ethanol and 3 ml of THF, and the mixture was stirred vigorously at atmospheric pressure under an atmosphere of hydrogen overnight. The reaction mixture was then filtered through kieselguhr and the filter residue was washed repeatedly with ethanol/THF. The combined filtrates were concentrated under reduced pressure and the residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1→10:1). This gave 1350 mg of the target product (80.6% of theory).

Workup

  1. filtrationThe reaction mixture was then filtered through kieselguhr
  2. washthe filter residue was washed repeatedly with ethanol/THF
  3. concentrationThe combined filtrates were concentrated under reduced pressure
  4. customthe residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1→10:1)

Sources & evidence

ORD record
ord-aff90de917e34b36b51d7b84013f2f40
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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