1,10-Phenanthroline → HCID 67017224, compound

HRID 2406203Notes

Reaction equation

HRID 2406203 reaction equation
IC1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][CH:3]=1.[C:9](=[O:14])([O-])[O:10][CH2:11][CH3:12].[N:15]1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].C[N:36]([CH3:39])C=O>[I+].[Cu+]>[CH3:8][C:5]1[CH:6]=[CH:7][C:39]([N:36]([C:9]([O:10][CH2:11][CH3:12])=[O:14])[NH2:15])=[CH:3][CH:4]=1

Participants

7

Reactant 5

HCID 13181,10-PhenanthrolineHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 122074-IodotolueneHCID 21226545CID 21226545

Product 1

HCID 67017224HCID 67017224, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 178505377HCID 178505377, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

N,N-Dimethylformamide (20 mL) was added to a mixture of 4-iodotoluene (3.0 g, 13.8 mmol), ethyl carbonate (1.72 g, 16.5 mmol), 1,10-phenanthroline (0.50 g, 2.76 mmol), copper(I) iodine (0.131 g, 0.69 mmol) and cesium carbonate (6.3 g, 19.3 mmol) and the mixture was heated under N2 at 80° C. for 18 h. The crude mixture was concentrated in vacuo and purified by chromatography on a silica gel column. Elution with n-heptane/EtOAc (4:1) as eluent afforded 10a as a white solid (2.22 g, 83%). mp. 35° C.,

Workup

  1. concentrationThe crude mixture was concentrated in vacuo
  2. custompurified by chromatography on a silica gel column
  3. washElution with n-heptane/EtOAc (4:1) as eluent

Sources & evidence

ORD record
ord-9a5a0e7e758e4c50a0362c18c49fc639
Source dataset
uspto-grants-2014_08
Patent number
US08809355B2

Reaction notes

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