Реакция #1710558

Уравнение реакции

2,6-dibromopyridine

(R)-6-oxaspiro[2.5]octan-1-amine hydrochloride

potassium carbonate

→

titled compound

Выход 88.3%

(R)-6-bromo-N-(6-oxaspiro[2.5]octan-1-yl)pyridin-2-amine

Выход 88.3%

Растворители

NMP

EtOAc

Условия реакции

Обработка

1. 1
   Температураto cool to ambient temperature
2. 2
   ПромывкаThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and brine
3. 3
   Сушкаdried over sodium sulfate
4. 4
   Фильтрацияfiltered off
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеThe resulting residue was purified by column chromatography [SiO2, 40 g, EtOAc/heptane=0/100 to 30/70]
7. 7
   Концентрированиеconcentrated in vacuo

Методика

To a solution of 2,6-dibromopyridine (200 mg, 0.84 mmol) in NMP (0.42 mL) was added (R)-6-oxaspiro[2.5]octan-1-amine hydrochloride (138 mg, 0.84 mmol) and potassium carbonate (350 mg, 2.53 mmol). The mixture was heated at 110° C. for 18 hr. The mixture was allowed to cool to ambient temperature and diluted with EtOAc. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water, and brine and dried over sodium sulfate, filtered off and concentrated in vacuo. The resulting residue was purified by column chromatography [SiO2, 40 g, EtOAc/heptane=0/100 to 30/70]. Pure fractions were combined and concentrated in vacuo giving 210 mg of titled compound. LCMS (m/z): 282.9/284.9 [M+H]+, retention time=0.85 min.

Источник