Triethylamine → HCID 44382361, compound

HRID 1727859Notes

Reaction equation

HRID 1727859 reaction equation
C(O[CH:5]([C:27]1[CH:32]=[CH:31][C:30]([C:33]([CH3:36])([CH3:35])[CH3:34])=[CH:29][CH:28]=1)[C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[CH:15][CH:14]=2)=[CH:8][CH:7]=1)(=O)C.C(N(CC)CC)C.[H][H]>CN(C)C=O.[OH-].[Pd+2].[OH-]>[C:33]([C:30]1[CH:31]=[CH:32][C:27]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([O:12][C:13]3[C:22]4[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=4)[N:16]=[CH:15][CH:14]=3)=[CH:8][CH:7]=2)=[CH:28][CH:29]=1)([CH3:36])([CH3:34])[CH3:35]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 57567586HCID 57567586, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 44382361HCID 44382361, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6228DimethylformamideSolvent

Procedure

(4-Tert-butylphenyl)-[4-(6,7-dimethoxy-4-quinolyloxy)phenyl]-methyl acetate (Compound 31) (26 mg) was dissolved in N,N-dimethylformamide (3 ml) to prepare a solution. Triethylamine (0.5 ml) and 20% palladium hydroxide (200 mg) were then added to the solution, and the mixture was stirred in a hydrogen atmosphere at room temperature for 2 hr. The reaction solution was filtered, water and ethyl acetate were added to the filtrate, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and was dried over sodium sulfate. The solvent was removed by evaporation under the reduced pressure to give the title compound (18 mg, yield 79%).

Workup

  1. customto prepare a solution
  2. filtrationThe reaction solution was filtered
  3. additionwater and ethyl acetate were added to the filtrate
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. customThe solvent was removed by evaporation under the reduced pressure

Sources & evidence

ORD record
ord-b5ff1541ccf541079cb461d2829af7df
Source dataset
uspto-grants-2009_02
Patent number
US07495104B2

Reaction notes

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