Реакция #1907326

Уравнение реакции

(2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine

sodium tert-butoxide

azacycloheptane

N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

N-(4-Bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

→

title compound

Выход 50.0%

N-(4-Azepan-1-yl-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide

Выход 50.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   КонцентрированиеThe reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL)
2. 2
   workup.ADDITIONwas added
3. 3
   Экстракцияthe product was extracted with isopropyl acetate (3×1.5 mL)
4. 4
   СушкаThe combined organic phases were dried over magnesium sulfate
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   Другоеpurified by flash chromatography

Методика

Bis(dibenzylideneacetone)palladium (2.8 mg) and (2′-dicyclohexylphosphanyl-biphenyl-2-yl)-dimethyl-amine (3.8 mg) were mixed in dry toluene (2.5 mL) under argon for 5 minutes. To this mixture were added sodium tert-butoxide (6 mg), azacycloheptane (7.5 mg) and N-(4-bromo-2,6-dimethyl-phenyl)-2-cyclopentyl-acetamide (1p, 15 mg) and the reaction was heated to 110° C. in a sealed 4 mL vial under argon for 48 hours. The reaction mixture was concentrated in vacuo, sodium hydroxide (2 M, 1.5 mL) was added and the product was extracted with isopropyl acetate (3×1.5 mL). The combined organic phases were dried over magnesium sulfate, concentrated in vacuo and purified by flash chromatography to furnish 7.9 mg (50% yield) of the title compound as an oil. LC-MS-TOF (m/z) 329 (MH+); tR=2.08, (UV, ELSD) 90%, 99%.

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