1,10-Phenanthroline → HCID 57550222, compound

HRID 1716866Notes

Reaction equation

[N:1]1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2[N:12]=[CH:11][CH:10]=[CH:9]3)C=C[CH:2]=1.N1C2C=CC=CC=2NC=1.[Br:24][C:25]1C=CC(I)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu](I)I>[Br:24][C:25]1[CH:9]=[CH:10][C:11]([N:12]2[C:13]3[CH:8]=[CH:7][CH:6]=[CH:5][C:14]=3[N:1]=[CH:2]2)=[CH:27][CH:26]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a mixture of copper iodide (0.16 g, 0.85 mmol) and 1,10-phenanthroline (0.31 g, 1.7 mmol) in anhydrous DMF (4.2 mL) was added benzimidazole (1.00 g, 8.5 mmol), 1-bromo-4-iodobenzene (2.88 g, 10.1 mmol), and cesium carbonate (5.53 g, 17 mmol) and the reaction mixture was heated to 110° C. and allowed to stir for 40 h. The reaction mixture was cooled to room temperature and the solvent was evaporated under reduced pressure. The residue was partitioned between water and dichloromethane and the organic layer was separated, dried (Na2SO4) and the solvent removed under reduced pressure. Purification by flash column chromatography (silica, petroleum ether:ethyl acetate 1:1) provided the title compound (64%). LCMS (ESI+) 274.2 (MH+).

Workup

temperatureThe reaction mixture was cooled to room temperature
customthe solvent was evaporated under reduced pressure
customThe residue was partitioned between water and dichloromethane
customthe organic layer was separated
dry with materialdried (Na2SO4)
customthe solvent removed under reduced pressure
customPurification by flash column chromatography (silica, petroleum ether:ethyl acetate 1:1)

Sources & evidence

ORD record: ord-5f7a69cbe5674b3f8d7c30870fbfd13d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07803825B2

Reaction notes

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