Реакция #86247

Уравнение реакции

(2,6-difluoro-4-pyridyl)boronic acid

3-Iodooxetane

Sodium hexamethyldisilazane

Trans-2-aminocyclohexanol hydrochloride

→

2,6-difluoro-4-(oxetan-3-yl)pyridine

Растворители

Isopropanol

EtOH

Isopropanol

Условия реакции

Обработка

1. 1
   ДругоеThe mixture was capped
2. 2
   Фильтрацияfiltered through Celite
3. 3
   ПромывкаThe filter cake was washed with EtOH (2×10 mL)
4. 4
   КонцентрированиеThe mixture was concentrated
5. 5
   Другоеthe residue was purified on silica
6. 6
   Промывкаeluted with 0 to 50% EtOAc in DCM

Методика

(2,6-difluoro-4-pyridyl)boronic acid (4.0004 mmol; 635.67 mg), Nickel(II) iodide (0.12001 mmol; 37.503 mg), Trans-2-aminocyclohexanol hydrochloride (0.12001 mmol; 18.382 mg), and Sodium hexamethyldisilazane (4.0004 mmol; 748.56 mg) were weighed into a CEM microwave vial. The mixture was capped then placed under a nitrogen atmosphere. Isopropanol (15 mL) was added and the mixture was stirred under nitrogen for 5 minutes. 3-Iodooxetane (2.0002 mmol; 368 mg) in Isopropanol (1.5 mL) was then added. The vial was heated at 100° C. under microwave for 20 minutes. The mixture was diluted with EtOH (15 mL) and filtered through Celite. The filter cake was washed with EtOH (2×10 mL). The mixture was concentrated and the residue was purified on silica eluted with 0 to 50% EtOAc in DCM to afford 2,6-difluoro-4-(oxetan-3-yl)pyridine (80.1 mg, 23%).

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