HCID 68107665, compound → HCID 68107570, compound

HRID 243803Notes

Reaction equation

HRID 243803 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N+:20]([O-])=O)[C:8]([O:18][CH3:19])=[C:9]([CH:11]([NH:16][CH3:17])[C:12]([F:15])([F:14])[F:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([C:5]1[CH:10]=[C:9]([CH:11]([NH:16][CH3:17])[C:12]([F:15])([F:14])[F:13])[C:8]([O:18][CH3:19])=[C:7]([CH:6]=1)[NH2:20])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 68107665HCID 68107665, compound

Product 1

HCID 68107570HCID 68107570, compoundYield 57.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1-(5-tert-butyl-2-methoxy-3-nitrophenyl)-2,2,2-trifluoro-N-methylethaneamine (0.413 g, 1.29 mmol) in methanol (12.0 mL), 10% palladium/activated charcoal (0.041 g) was added and the resulting mixture was stirred at room temperature under hydrogen atmosphere for 3 hours. After completion of the reaction, the insoluble materials were filtered through a Celite pad, and the solvent was evaporated under reduced pressure. The obtained residue was purified by column chromatography (amine coated silica gel, hexane/ethyl acetate=90/10-0/100) to obtain 0.215 g of the captioned compound (57% yield).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe insoluble materials were filtered through a Celite pad
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by column chromatography (amine coated silica gel, hexane/ethyl acetate=90/10-0/100)

Sources & evidence

ORD record
ord-b0b56fdb670440dab17e97f436c891f1
Source dataset
uspto-grants-2014_02
Patent number
US08653304B2

Reaction notes

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