反应详情

温度

50 °C

Ethyl 4-fluoro-2-hydroxy-5-iodobenzoate (3.6 g, 80%, 10 mmol), 4-ethynyl-N-(3-methyl-2-pyridinyl)benzenesulfonamide (2.7 g, 10 mmol) and triethylamine (5 g, 50 mmol) were suspended in tetrahydrofuran (20 ml) and the mixture heated to 50° C. Dichlorobis(triphenylphosphine)palladium (45 mg, 0.06 mmol) and copper(I)iodide (76 mg, 0.4 mmol) were added with stirring. After about 15 min a practically clear solution had formed. After 3 h at 50° C. the solution was taken to dryness and triturated with isobutylmethylketone and dilute hydrochloric acid. The organic phase was separated and the solvent evaporated. The oily residue was triturated with a small amount of acetonitrile to form crystals. These were recrystallized from acetic acid. The product was dissolved in a small amount of chloroform and the solution applied on top of a short silica gel column and eluted with 25% isobutylmethylketone in toluene. The pure product resulted after evaporation of the solvent. Yield 2.0 g, 44%.

1. customAfter about 15 min a practically clear solution had formed
2. customtriturated with isobutylmethylketone and dilute hydrochloric acid
3. customThe organic phase was separated
4. customthe solvent evaporated
5. customThe oily residue was triturated with a small amount of acetonitrile
6. customto form crystals
7. customThese were recrystallized from acetic acid
8. dissolutionThe product was dissolved in a small amount of chloroform
9. washeluted with 25% isobutylmethylketone in toluene
10. customThe pure product resulted
11. customafter evaporation of the solvent