HCID 57633726, compound → HCID 57633720, compound

HRID 2109099Notes

Reaction equation

HRID 2109099 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:15][C:16](=[CH2:21])[C:17]([O:19][CH3:20])=[O:18])[CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]=1[C:22]([F:25])([F:24])[F:23])#[N:2]>CCOC(C)=O.[Pd]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:10][C:11]([F:14])([F:13])[F:12])[CH2:15][CH:16]([CH3:21])[C:17]([O:19][CH3:20])=[O:18])=[CH:5][C:4]=1[C:22]([F:23])([F:25])[F:24])#[N:2]

Participants

4

Reactant 1

HCID 57633726HCID 57633726, compound

Product 1

HCID 57633720HCID 57633720, compoundYield 62.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A suspension of 5% Pd/C (0.060 g) in EtOAc (3 mL) was stirred under an H2 atmosphere (balloon pressure) for 15 min. A solution of methyl 2-{[[4-cyano-3-(trifluoromethyl)phenyl](2,2,2-trifluoroethyl)amino]methyl}acrylate (0.090 g, 0.245 mmol) in EtOAc (3 mL) was added and the mixture stirred for 1 hr. The catalyst was filtered off and washed with EtOAc. The filtrate was concentrated and purified by silica gel chromatography to afford 0.056 g (62% yield) of the title compound: MS (ES) m/z 369 (M+1).

Workup

  1. stirringthe mixture stirred for 1 hr
  2. filtrationThe catalyst was filtered off
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-3f4526bd458f46558053ebc71e8c6f7d
Source dataset
uspto-grants-2009_04
Patent number
US07514470B2

Reaction notes

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