8-Hydroxyquinoline → HCID 86700748, compound

HRID 2272542Notes

Reaction equation

HRID 2272542 reaction equation
Br[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](C(C)C)=[N:5][N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1.Cl.[NH:24]1[CH:28]=[C:27]([C:29]2[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=2)[N:26]=[CH:25]1.N1C2C(=CC=CC=2O)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.[Cu-]=O>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:6]2[C:7]3[C:3](=[C:2]([N:24]4[CH:28]=[C:27]([C:29]5[CH:30]=[N:31][CH:32]=[CH:33][CH:34]=5)[N:26]=[CH:25]4)[CH:10]=[CH:9][CH:8]=3)[CH:4]=[N:5]2)=[CH:17][CH:16]=1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 86700749HCID 86700749, compoundHCID 178478280HCID 178478280, compound

Product 1

HCID 86700748HCID 86700748, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

A solution of the colorless oily substance (4-bromo-3-(isopropyl)-1-(4-methoxybenzyl)-1H-indazole) (2.4 g), 3-(1H-imidazol-4-yl)pyridine hydrochloride (1.75 g), copper(I) oxide (96 mg), poly(ethylene glycol) (1.34 g), 8-quinolinol (194 mg), and cesium carbonate (8.7 g) in DMSO (22 mL) was stirred overnight under heating at 125° C. After completion of the reaction, the reaction solution was allowed to standing still for cooling, filtered, and the filtrate was partitioned between ethyl acetate and water. The organic layer was washed with saturated brine and dried by the addition of anhydrous sodium sulfate. After removal of the solvent by evaporation, the residue was purified by neutral silica gel column chromatography (chloroform/ethyl acetate/methanol) to obtain 3-isopropyl-1-(4-methoxybenzyl-4-(4-(pyridin-3-yl)-1H-imidazol-1-yl)-1H-indazole (710 mg, yield 250) as a yellow oily substance.

Workup

  1. customAfter completion of the reaction
  2. temperaturefor cooling
  3. filtrationfiltered
  4. customthe filtrate was partitioned between ethyl acetate and water
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried by the addition of anhydrous sodium sulfate
  7. customAfter removal of the solvent
  8. customby evaporation
  9. customthe residue was purified by neutral silica gel column chromatography (chloroform/ethyl acetate/methanol)

Sources & evidence

ORD record
ord-26b6057dd28049f28910fd8877214a8d
Source dataset
uspto-grants-2015_09
Patent number
US09120780B2

Reaction notes

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