Potassium Carbonate → HCID 67458282, compound

HRID 1922154Notes

Reaction equation

HRID 1922154 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([CH:12]([CH3:14])[CH3:13])[C:8]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([N:22]4[CH:26]=[CH:25][CH:24]=[N:23]4)=[CH:18][CH:17]=3)=[C:7]([CH3:27])[C:6]=2[C:5]([OH:28])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:35][O:36][C:37](=[O:40])[CH2:38]Br>CC(C)=O>[CH3:35][O:36][C:37](=[O:40])[CH2:38][O:28][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[C:11]2[C:6]=1[C:7]([CH3:27])=[C:8]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]3[CH:26]=[CH:25][CH:24]=[N:23]3)=[CH:18][CH:17]=1)[C:9]([CH:12]([CH3:13])[CH3:14])=[N:10]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 136348361HCID 136348361, compound

Product 1

HCID 67458282HCID 67458282, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 8-chloro-2-isopropyl-4-methyl-3-(4-pyrazol-1-ylbenzyl)quinolin-5-ol (0.10 g), acetone (3.0 mL), potassium carbonate (0.035 g) and bromoacetic acid methyl ester (0.025 mL) was stirred at room temperature for 20 hours. The mixture was concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase was dried over magnesium sulfate and concentrated under reduced pressure. Purification of the residue by column chromatography on silica gel, eluting with a mixture of cyclohexane and ethyl acetate (10:0 to 8:2 by volume) gave title compound as colourless oil (0.087 g).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by column chromatography on silica gel
  6. washeluting with a mixture of cyclohexane and ethyl acetate (10:0 to 8:2 by volume)

Sources & evidence

ORD record
ord-9e1954dbfa334523ae37827892c55a2e
Source dataset
uspto-grants-2012_05
Patent number
US08173812B2

Reaction notes

Loading…