1,10-Phenanthroline → HCID 67420602, compound

HRID 2219302Notes

Reaction equation

HRID 2219302 reaction equation
N1[C:14]2[C:5](=[CH:6][CH:7]=[C:8]3[C:13]=2N=CC=C3)C=CC=1.C(=CC(C=CC1C=CC=CC=1)=O)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH:39]1[CH:43]=[C:42]([C:44]2[C:45]([C:50]3[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=3)=[N:46][O:47][C:48]=2[CH3:49])[N:41]=[CH:40]1.IC1C=CC=CC=1.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:49][C:48]1[O:47][N:46]=[C:45]([C:50]2[CH:51]=[CH:52][CH:53]=[CH:54][CH:55]=2)[C:44]=1[C:42]1[N:41]=[CH:40][N:39]([C:5]2[CH:14]=[CH:13][CH:8]=[CH:7][CH:6]=2)[CH:43]=1

Participants

8

Reactant 6

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 11575IodobenzeneHCID 25517Ammonium ChlorideHCID 95417Dibenzylidene acetoneHCID 178434980HCID 178434980, compound

Product 1

HCID 67420602HCID 67420602, compoundYield 13.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of copper(I) trifluoromethanesulfonate benzene complex (12.3 mg, 0.22 mmol), 1,10-phenanthroline (79.5 mg, 0.44 mmol), dibenzylideneacetone (5.2 mg, 0.22 mmol) and cesium carbonate (144 mg, 0.44 mmol) was added a suspension of 4-(1H-imidazol-4-yl)-5-methyl-3-phenyl-isoxazole (149 mg, 0.6 mmol) in toluene (2 mL) followed by iodobenzene (90 mg, 0.44 mmol) and the resulting mixture heated at 120° C. for 2 days. After cooling to room temperature the resulting mixture was poured into aqueous ammonium chloride (saturated) and extracted with ethyl acetate. The organic extracts were then dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:1) afforded the title compound (18 mg, 13%) which was obtained as a light brown gum. MS: m/e=302.1 [M+H]+.

Workup

  1. additionwas added
  2. temperatureAfter cooling to room temperature the resulting mixture
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were then dried over sodium sulphate
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-89d4a4247e1d48be8649890cf6ee8d17
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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