4-[[3,5-Bis(trimethylsilyl)benzoyl]amino]-2-fluorocinnamic acid → HCID 59446279, compound

HRID 2265094Notes

Reaction equation

HRID 2265094 reaction equation
[CH3:1][Si:2]([CH3:29])([CH3:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])[CH:23]=1)[C:6]([NH:8][C:9]1[CH:19]=[CH:18][C:12]([CH:13]=[CH:14][C:15]([OH:17])=[O:16])=[C:11]([F:20])[CH:10]=1)=[O:7].[H][H]>O1CCCC1.CO.[C].[Pd]>[CH3:27][Si:24]([CH3:25])([CH3:26])[C:22]1[CH:21]=[C:5]([CH:4]=[C:3]([Si:2]([CH3:29])([CH3:28])[CH3:1])[CH:23]=1)[C:6]([NH:8][C:9]1[CH:19]=[CH:18][C:12]([CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[C:11]([F:20])[CH:10]=1)=[O:7]

Participants

6

Reactant 2

HCID 684821214-[[3,5-Bis(trimethylsilyl)benzoyl]amino]-2-fluorocinnamic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 59446279HCID 59446279, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound 2 (160 mg) was dissolved in a mixed solution of tetrahydrofuran (0.59 ml) and methanol (0.59 ml). Palladium carbon (4.4 mg) was added thereto, and the mixture was stirred in a hydrogen atmosphere for 4.5 hours. After the reaction was over, the reaction mixture was filtered through Celite. The filtrate was condensed and recrystallized with dichloromethane and n-hexane to obtain Compound 7 (122 mg, 76%) as a white solid.

Workup

  1. filtrationwas filtered through Celite
  2. customcondensed
  3. customrecrystallized with dichloromethane and n-hexane

Sources & evidence

ORD record
ord-37ee053aeefe4ab994f6f1b651f7b03f
Source dataset
uspto-grants-2010_12
Patent number
US07855300B2

Reaction notes

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