Potassium Carbonate → HCID 67421646, compound

HRID 2219335Notes

Reaction equation

HRID 2219335 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]2[N:14]=[CH:15][NH:16][CH:17]=2)=[C:11]([CH3:18])[O:10][N:9]=1.I[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1.N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.[Cu]I.O>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([C:13]2[N:14]=[CH:15][N:16]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=3)[CH:17]=2)=[C:11]([CH3:18])[O:10][N:9]=1

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 696764-IodoanisoleHCID 145742L-ProlineHCID 178434991HCID 178434991, compound

Product 1

HCID 67421646HCID 67421646, compoundYield 4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-(2-fluoro-phenyl)-4-(1H-imidazol-4-yl)-5-methyl-isoxazole (100 mg, 0.41 mmol) in DMSO (2 mL) was added copper(I) iodide (7.9 mg, 0.04 mmol), 4-iodoanisole (57 mg, 0.45 mmol), L-proline (9.5 mg, 0.08 mmol) and potassium carbonate (113.6 mg, 0.82 mmol) and the resulting mixture heated at 90° C. for 3 days. After cooling to room temperature the resulting mixture was poured into water and extracted with ethyl acetate. The organic extracts were then washed with water and brine, dried over sodium sulphate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=1:1) afforded the title compound (5.7 mg, 4%) which was obtained as a light brown gum. MS: m/e=350.5 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature the resulting mixture
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were then washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customPurification by chromatography (SiO2, heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-fd34a5622c464c599f4fc1768f1df3d9
Source dataset
uspto-grants-2008_08
Patent number
US07414061B2

Reaction notes

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