Potassium Carbonate → ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzoate

HRID 384445

Reaction equation

HRID 384445 reaction equation
[CH2:1]([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:22]=[C:23]([CH:29]=[C:30]([OH:32])[CH:31]=2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]=1[CH3:33])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:35][CH:36]1[CH2:41][CH2:40][O:39][CH2:38][CH2:37]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([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:22]=[C:23]([CH:29]=[C:30]([O:32][CH2:35][CH:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH:31]=2)[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:10]=1[CH3:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 59527065HCID 59527065, compound

Product 1

HCID 59527401ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzoateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-hydroxybenzoate (2.10 g), 4-(bromomethyl)tetrahydro-2H-pyrane (2.29 g), potassium carbonate (0.98 g), and DMF (40 mL) was stirred at 80° C. for 13 hours. The reaction mixture was concentrated under reduced pressure, and then water was added to the residue, followed by extraction with ethyl acetate (150 mL). The organic layer was washed sequentially with water and saturated brine, and dried. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1) to obtain ethyl 3-{[4-(benzyloxy)-3-methylquinolin-2-yl]methoxy}-5-(tetrahydro-2H-pyran-4-ylmethoxy)benzoate (2.50 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionwater was added to the residue
  3. extractionfollowed by extraction with ethyl acetate (150 mL)
  4. washThe organic layer was washed sequentially with water and saturated brine
  5. customdried
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (eluent: chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-2e07592495294ee89e1737827a91f1e2
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Linked notes

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