3-Cyclopent-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine → 5-Cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamine

HRID 1253777Notes

Reaction equation

HRID 1253777 reaction equation
[C:1]1([C:6]2[C:7]([O:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[N:8][CH:9]=[C:10]([N+:12]([O-])=O)[CH:11]=2)[CH2:5][CH2:4][CH2:3][CH:2]=1>C(OCC)(=O)C.[Pd]>[CH:1]1([C:6]2[CH:11]=[C:10]([NH2:12])[CH:9]=[N:8][C:7]=2[O:15][CH2:16][C:17]([F:18])([F:19])[F:20])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 1

HCID 712942943-Cyclopent-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine

Product 1

HCID 712941725-Cyclopentyl-6-(2,2,2-trifluoro-ethoxy)-pyridin-3-ylamineYield 69.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-cyclopent-1-enyl-5-nitro-2-(2,2,2-trifluoro-ethoxy)-pyridine (Example 1b) (600 mg, 2.08 mmol) in ethyl acetate (30 mL) was added 10% Pd/C (554 mg, 0.52 mmol) under argon atmosphere. The reaction mixture was stirred under hydrogen balloon pressure for 12 h. The catalyst was filtered off and the filtrate was concentrated under reduced pressure. The crude thus obtained was purified by column chromatography (Combi-Flash, 40 g, 25% ethyl acetate/hexane) to get the title compound (375 mg, 69.16%) as colorless liquid; MS (ESI): 259 [M−H]−.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe crude thus obtained
  4. customwas purified by column chromatography (Combi-Flash, 40 g, 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39468a9e4dd149d5925ad3d06c84dc84
Source dataset
uspto-grants-2013_06
Patent number
US08455501B2

Reaction notes

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