HCID 22448927, compound → HCID 22448978, compound

HRID 2186738Notes

Reaction equation

HRID 2186738 reaction equation
[O:1]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH:11]=[CH:12][CH:13]=[N:14]2)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3].[H][H]>C(O)C.[Pd]>[O:1]([C:9]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:10]=1[CH2:11][CH2:12][CH2:13][NH:14]2)[Si:2]([C:5]([CH3:8])([CH3:7])[CH3:6])([CH3:4])[CH3:3]

Participants

5

Reactant 2

HCID 22448927HCID 22448927, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 22448978HCID 22448978, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

5-(t-butyldimethylsiloxy)quinoline (1715 mg) was dissolved in ethanol (50 ml), and the air in a reactor was substituted by argon. 10% Pd—C (100 mg) was added to the resultant solution, and the mixture was stirred at room temperature in the reactor in which the atmosphere was replaced by hydrogen. After disappearance of the raw materials was confirmed, the solid was filtered off, and the filtrate was concentrated. The resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=10/1) to obtain the object compound (1426 mg, yield 82%).

Workup

  1. customthe air in a reactor was substituted by argon
  2. filtrationthe solid was filtered off
  3. concentrationthe filtrate was concentrated
  4. customThe resultant residue was purified by column chromatography (silica gel:hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-61553091cf65417ba8ed2f6702d9edca
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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