1,10-Phenanthroline → HCID 66893394, compound

HRID 1162002Notes

Reaction equation

HRID 1162002 reaction equation
I[C:2]1[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.[OH:14][CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>[Cu]I.C1(C)C=CC=CC=1>[N+:11]([C:4]1[CH:3]=[C:2]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:10]2[O:9][CH:8]=[CH:7][C:6]=2[CH:5]=1)([O-:13])=[O:12]

Participants

7

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 611632-MorpholinoethanolHCID 21864764HCID 21864764, compound

Product 1

HCID 66893394HCID 66893394, compoundYield 32%

Reagents, catalysts & solvents 2

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

Procedure

To a test tube was added 7-iodo-5-nitrobenzofuran (1.0 g, 0.00346 mol), 4-(2-hydroxyethyl)morpholine (0.91 g, 0.00692 mol), cesium carbonate (2.25 g, 0.00692 mol), 1,10-phenanthroline (0.25 g, 0.00138 mol) and CuI (130 mg, 0.692 mmol). Toluene (15 mL) was added and the solution was heated in a StemBlock for 72 h. After filtration through Celite, the crude material was purified by flash chromatography (EtOAc/DCM; 1:1). Yield: 32%, HPLC purity=90%, m/z=293 (M+H)+.

Workup

  1. temperaturethe solution was heated in a StemBlock for 72 h
  2. filtrationAfter filtration through Celite
  3. customthe crude material was purified by flash chromatography (EtOAc/DCM; 1:1)

Sources & evidence

ORD record
ord-b51935799562419bb04cb2de739004f6
Source dataset
uspto-grants-2010_10
Patent number
US07820675B2

Reaction notes

Loading…