2-Cyclopropyl-7-fluoro-5-methyl-6-vinyl-1,3-benzoxazole-4-carbonitrile → HCID 68584694, compound

HRID 17459Notes

Reaction equation

HRID 17459 reaction equation
[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:17]#[N:18])[C:10]([CH3:16])=[C:11]([CH:14]=[CH2:15])[C:12]=3[F:13])[N:8]=2)[CH2:3][CH2:2]1.[H][H]>C(OCC)(=O)C.[C].[Pd]>[CH:1]1([C:4]2[O:5][C:6]3[C:7](=[C:9]([C:17]#[N:18])[C:10]([CH3:16])=[C:11]([CH2:14][CH3:15])[C:12]=3[F:13])[N:8]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 685849162-Cyclopropyl-7-fluoro-5-methyl-6-vinyl-1,3-benzoxazole-4-carbonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 68584694HCID 68584694, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-Cyclopropyl-7-fluoro-5-methyl-6 vinyl-1,3-benzoxazole-4-carbonitrile (I-180) (114 mg, 0.47 mmol) was dissolved in ethyl acetate (2.5 ml), then at room temperature, 10% palladium-carbon (23 mg) was added. The suspension was stirred at the same temperature under atmospheric pressure of hydrogen for 16 hours. The catalyst was separated by filtration with washing with ethyl acetate, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative TLC (eluent, ethyl acetate:hexane=1:2) to obtain the entitled compound (110 mg, 96%) as a white solid.

Workup

  1. customThe catalyst was separated by filtration
  2. washwith washing with ethyl acetate
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative TLC (eluent, ethyl acetate:hexane=1:2)

Sources & evidence

ORD record
ord-8011dc56df7d496889cdf8b0c4791aa8
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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