Tetrahydrofuran → HCID 66810488, compound

HRID 1097530Notes

Reaction equation

HRID 1097530 reaction equation
[C:1]([C:3]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:4]=1[O:5][C:6]1[CH:7]=[CH:8][C:9]([F:26])=[C:10]([NH:12][C:13](=[O:25])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH:11]=1)#[N:2].O1CCCC1>C(O)C.[C].[Pd]>[NH2:31][C:29]1[CH:28]=[CH:27][C:4]([O:5][C:6]2[CH:7]=[CH:8][C:9]([F:26])=[C:10]([NH:12][C:13](=[O:25])[CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[CH:16]=3)[CH:11]=2)=[C:3]([C:1]#[N:2])[CH:30]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66810481HCID 66810481, compound

Product 1

HCID 66810488HCID 66810488, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-[5-(2-cyano-4-nitrophenoxy)-2-fluorophenyl]-2-[3-(trifluoromethyl)phenyl]acetamide (1.36 g, 2.96 mmol) in ethanol (25 mL)/tetrahydrofuran (10 mL) was added 10% palladium-carbon (160 mg), and the mixture was stirred at room temperature for 5 hr under a hydrogen atmosphere (1 atm). Insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0), and the fraction containing the object product was concentrated under reduced pressure to give the title compound (1.17 g, 92%) as a beige amorphous form.

Workup

  1. filtrationInsoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe obtained residue was purified by basic silica gel column chromatography (ethyl acetate/n-hexane=30/70→100/0)
  4. additionthe fraction containing the object product
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-3efbea28dba445f2bb657ff4452bc841
Source dataset
uspto-grants-2012_03
Patent number
US08143258B2

Reaction notes

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