1,10-Phenanthroline → HCID 68727207, compound

HRID 408650Notes

Reaction equation

HRID 408650 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9](I)[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][OH:21])[CH:15]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.O.[Cu]I>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:21][CH2:20][C:16]3[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=3)[CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1

Participants

8

Reactant 4

HCID 13181,10-PhenanthrolineHCID 75103-PyridinemethanolHCID 10796Cesium carbonateHCID 43668381HCID 43668381, compound

Product 1

HCID 68727207HCID 68727207, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-Chloro-6-iodo-2-methylquinoline (0.61 g; see Preparation 6(ii) below), 3-pyridyl-carbinol (0.26 g), copper (I) iodide (0.038 g), caesium carbonate (0.78 g), 1,10-phenanthroline (0.072 g) in toluene (3 mL) was heated in a microwave at 160° C. for 40 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica eluting with a mixture of methanol and dichloromethane. Evaporation of the desired fractions gave the title compound as a pale pink solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by chromatography on silica eluting with a mixture of methanol and dichloromethane
  7. customEvaporation of the desired fractions

Sources & evidence

ORD record
ord-a0504e92c8484e898c5f3e0feb3cbeb7
Source dataset
uspto-grants-2014_06
Patent number
US08759348B2

Reaction notes

Loading…