HCID 104700261, compound → 1236284-92-6

HRID 56621Notes

Reaction equation

HRID 56621 reaction equation
[F:1][C:2]1[CH:14]=[C:13]([N+:15]([O-])=O)[C:12]([F:18])=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5]>O1CCCC1.C(OCC)(=O)C.[Pd]>[NH2:15][C:13]1[C:12]([F:18])=[CH:11][C:3]([C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[C:2]([F:1])[CH:14]=1

Participants

5

Reactant 1

HCID 104700261HCID 104700261, compound

Product 1

HCID 580578441236284-92-6

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1000 mg (2.82 mmol) of tert-butyl 2,5-difluoro-4-nitrobenzoate in 8 ml of tetrahydrofuran and 8 ml of ethyl acetate was hydrogenated in the presence of 65.6 mg of palladium (10% on activated carbon) at RT and standard pressure. The reaction mixture was then filtered through Celite and the filtrate was concentrated under reduced pressure and dried. The crude product was purified by normal phase chromatography (mobile phase: cyclohexane/ethyl acetate 15%-20% mixtures). Yield: 155 mg (purity 85%, 20% of theory)

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customdried
  4. customThe crude product was purified by normal phase chromatography (mobile phase: cyclohexane/ethyl acetate 15%-20% mixtures)

Sources & evidence

ORD record
ord-d64eab8bf2004c5f897bd6daf3c9a8ec
Source dataset
uspto-grants-2016_09
Patent number
US09434690B2

Reaction notes

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