Water → HCID 70559854, compound

HRID 408594Notes

Reaction equation

HRID 408594 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([NH2:9])[CH:6]=[CH:7][CH:8]=1.Br[CH2:13][CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.CCOC(C)=O>[CH2:19]([O:18][C:16](=[O:17])[CH2:15][CH2:14][CH2:13][NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=1)[CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 73753-(Trifluoromethyl)anilineHCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrate

Product 1

HCID 70559854HCID 70559854, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3-trifluoromethyl-phenylamine (1 eq.) and ethyl 4-bromobutyrate (2 eq.) in DMF were added K2CO3 (3 eq.) and KI (cat.). The mixture was heated at 100° C. for 16 h, water and EtOAc were added, the organic layer was washed with water, brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 90/10 to 70/30) to afford 4-(3-trifluoromethyl-phenylamino)-butyric acid ethyl ester as a yellow oil.

Workup

  1. washthe organic layer was washed with water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was purified by chromatography on silica gel (elution with heptane/EtOAc: 90/10 to 70/30)

Sources & evidence

ORD record
ord-bda02a04402a4b209a53c9bf2c7fb12b
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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