Tetrahydrofuran → HCID 66810289, compound

HRID 455244Notes

Reaction equation

HRID 455244 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][C:3]=1[NH:22][C:23](=[O:35])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=1.O1CCCC1>CO.[C].[Pd]>[NH2:17][C:14]1[CH:15]=[CH:16][C:7]([O:6][C:5]2[CH:20]=[CH:21][C:2]([F:1])=[C:3]([NH:22][C:23](=[O:35])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[CH:26]=3)[CH:4]=2)=[C:8]([CH:13]=1)[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 66810464HCID 66810464, compound

Product 1

HCID 66810289HCID 66810289, compoundYield 87.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

To a solution of methyl 2-[4-fluoro-3-({[3-(trifluoromethyl)phenyl]acetyl}amino)phenoxy]-5-nitrobenzoate (3.75 g, 7.62 mmol) in methanol (40 mL)/tetrahydrofuran (8 mL) solution was added 10% palladium-carbon (400 mg), and the mixture was stirred at room temperature for 6 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→80/20), and the fraction containing the object product was concentrated under reduced pressure to give the title compound (3.09 g, 87%) as a yellow oil.

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→80/20)
  4. additionthe fraction containing the object product
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-e54c6bc4cb7f4a46ba3ab8bf57b8cf36
Source dataset
uspto-grants-2013_07
Patent number
US08497274B2

Reaction notes

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