HCID 67059672, compound → HCID 67059665, compound

HRID 1807772Notes

Reaction equation

HRID 1807772 reaction equation
C([NH:8][C:9]1[C:18]([F:19])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Br:20])[CH:10]=1)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd].CO>[NH2:8][C:9]1[C:18]([F:19])=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([Br:20])[CH:10]=1

Participants

6

Reactant 2

HCID 67059672HCID 67059672, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67059665HCID 67059665, compoundYield 73.8%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A suspension of the methyl 4-(benzylamino)-2-bromo-5-fluorobenzoate (2.4 g, 7.10 mmol) in acetic acid was treated with 10% palladium on charcoal (250 mg) and stirred at room temperature under 2 bar hydrogen for 18 hours. The reaction mixture was then diluted with methanol, filtered through celite and evaporated to low volume. The residue was suspended in water (50 mL) and basified with 5% sodium carbonate solution then was extracted with ethyl acetate (2×). The combined organic phases were dried (sodium sulfate) and evaporated to a sandy solid. This crude solid was dissolved in the methanol and passed down an SCX cartridge. Evaporation of the methanol eluents gave the title compound (1.3 g).

Workup

  1. filtrationfiltered through celite
  2. customevaporated to low volume
  3. extractionthen was extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic phases were dried (sodium sulfate)
  5. customevaporated to a sandy solid
  6. dissolutionThis crude solid was dissolved in the methanol
  7. customEvaporation of the methanol eluents

Sources & evidence

ORD record
ord-d08cd76ff43341bea971fb88f4e1bfd8
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

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