HCID 59526897, compound → HCID 25222164, compound

HRID 384484Notes

Reaction equation

HRID 384484 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11]([CH2:19][O:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)[CH:22]=2)[C:10]=1[CH3:35])C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[CH3:35][C:10]1[C:9](=[O:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[CH2:19][O:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][CH:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)[CH:22]=1

Participants

4

Reactant 1

HCID 59526897HCID 59526897, compound

Product 1

HCID 25222164HCID 25222164, compoundYield 77.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 4-(benzyloxy)-3-methyl-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}quinoline (330 mg) in ethanol-THF (1:1, 10 mL) was added 10% palladium-activated carbon (80 mg), and the mixture was stirred at room temperature under hydrogen atmosphere for 1 hour. The catalyst was removed by filtration, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 3-methyl-2-{[3-(tetrahydro-2H-pyran-4-ylmethoxy)phenoxy]methyl}quinolin-4(1H)-one (207 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-59e5cc47d41e4346b089d9cbb6c27d09
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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