8-Hydroxyquinoline → isopropyl 5-(4-cyclopropyl-1H-imidazol-1-yl)-2-methoxy-benzoate

HRID 1423336Notes

Reaction equation

HRID 1423336 reaction equation
I[C:2]1[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:13]=1)[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8].[CH:16]1([C:19]2[N:20]=[CH:21][NH:22][CH:23]=2)[CH2:18][CH2:17]1.OC1C=CC=C2C=1N=CC=C2.C(=O)([O-])[O-].[Cs+].[Cs+]>[Cu-]=O.C(#N)CCC>[CH:16]1([C:19]2[N:20]=[CH:21][N:22]([C:2]3[CH:3]=[CH:4][C:5]([O:14][CH3:15])=[C:6]([CH:13]=3)[C:7]([O:9][CH:10]([CH3:12])[CH3:11])=[O:8])[CH:23]=2)[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 19238-HydroxyquinolineHCID 10796Cesium carbonateHCID 58035637Isopropyl 5-iodo-2-methoxybenzoateHCID 178420870HCID 178420870, compound

Product 1

HCID 58035659isopropyl 5-(4-cyclopropyl-1H-imidazol-1-yl)-2-methoxy-benzoateYield 51%

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 8008ButyronitrileSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of isopropyl 5-iodo-2-methoxybenzoate (1.52 g, 4.75 mmol), 4-cyclopropyl-1H-imidazole (0.777 g, 7.13 mmol), copper(I) oxide (0.067 g, 0.047 mmol), 8-hydroxyquinoline (0.103 g, 0.71 mmol), cesium carbonate (2.41 g, 7.41 mmol), PEG-3350 (1.18 g) and butyronitile (60 ml) was placed in a sealed tube, which was flushed with nitrogen and heated at 120° C. for 16 hours. The solvent was removed under reduced pressure, and the residue was purified by reversed phase HPLC to provide isopropyl 5-(4-cyclopropyl-1H-imidazol-1-yl)-2-methoxybenzoate. (0.720 g, 2.4 mmol). 51% yield. 301 (M+1).

Workup

  1. customwas placed in a sealed tube
  2. customwhich was flushed with nitrogen
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by reversed phase HPLC

Sources & evidence

ORD record
ord-0991a5348b994477b3ca8d4b1e05e6d4
Source dataset
uspto-grants-2015_01
Patent number
US08927582B2

Reaction notes

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