Potassium Carbonate → 2-[4-(6-Chloroquinolin-2-yloxy)-2,6-dimethylphenyl]-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

HRID 1193041Notes

Reaction equation

HRID 1193041 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]2=[O:22])=[C:4]([CH3:23])[CH:3]=1.Cl[C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([Cl:35])[CH:31]=2)[N:26]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:35][C:30]1[CH:31]=[C:32]2[C:27](=[CH:28][CH:29]=1)[N:26]=[C:25]([O:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([CH:9]3[C:13](=[O:14])[CH:12]([CH2:15][CH:16]4[CH2:21][CH2:20][O:19][CH2:18][CH2:17]4)[CH2:11][C:10]3=[O:22])=[C:6]([CH3:8])[CH:7]=1)[CH:34]=[CH:33]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6075022,6-DichloroquinolineHCID 667096322-(4-Hydroxy-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

Product 1

HCID 667097362-[4-(6-Chloroquinolin-2-yloxy)-2,6-dimethylphenyl]-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of 2-(4-hydroxy-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione (0.104 g, 0.00033 mol), 2,6-dichloroquinoline (0.065 g, 0.00033 mol) and potassium carbonate (0.140 g, 0.00101 mol) in anhydrous N,N-dimethylformamide (3 ml) is heated at 140° C. for 40 minutes under microwave irradiation. After cooling to room temperature the reaction mixture was quenched with 2M hydrochloric acid and extracted with ethyl acetate. The organic phase is separated, washed with distilled water then dried over anhydrous magnesium sulfate. The mixture is filtered, the filtrate is evaporated in vacuo and the residue is purified by preparative reverse phase HPLC to afford 2-[4-(6-chloroquinolin-2-yloxy)-2,6-dimethylphenyl]-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione.

Workup

  1. temperatureAfter cooling to room temperature the reaction mixture
  2. customwas quenched with 2M hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. customThe organic phase is separated
  5. washwashed with distilled water
  6. dry with materialthen dried over anhydrous magnesium sulfate
  7. filtrationThe mixture is filtered
  8. customthe filtrate is evaporated in vacuo
  9. customthe residue is purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-332ffd047b734ef4b59143045eb94861
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

Loading…