HCID 59527100, compound → HCID 25254173, compound

HRID 384486Notes

Reaction equation

HRID 384486 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]=[C:25]([O:27][CH2:28][CH2:29][C:30]([CH3:33])([OH:32])[CH3:31])[CH:24]=[CH:23][N:22]=2)[C:10]=1[CH3:34])C1C=CC=CC=1>C(O)C.C1COCC1.[Pd]>[OH:32][C:30]([CH3:33])([CH3:31])[CH2:29][CH2:28][O:27][C:25]1[CH:24]=[CH:23][N:22]=[C:21]([O:20][CH2:19][C:11]2[NH:12][C:13]3[C:18]([C:9](=[O:8])[C:10]=2[CH3:34])=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:26]=1

Participants

4

Reactant 1

HCID 59527100HCID 59527100, compound

Product 1

HCID 25254173HCID 25254173, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

To a solution of 4-[(2-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}pyridin-4-yl)oxy]-2-methyl butan-2-ol (1.33 g) in ethanol-THF (1:4, 45 mL) was added 10% palladium-activated carbon (300 mg) under nitrogen atmosphere. The mixture was placed under hydrogen atmosphere, and then stirred at room temperature for 1 hour. The catalyst was removed by filtration, and then the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=97/3) to obtain 2-({[4-(3-hydroxy-3-methylbutoxy)pyridin-2-yl]oxy}methyl)-3-methylquinolin-4(1H)-one (783 mg) as a crystal.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform/methanol=97/3)

Sources & evidence

ORD record
ord-f2897b9d81334aa79b7ad44d4e9246a7
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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