Реакция #423758

Уравнение реакции

1-bromo-3-(bromomethyl)-adamantane

4-iodopyrazole

sodium hydride

→

title compound

1-[(3-bromotricyclo[3.3.1.13,7]dec-1-yl)methyl]-4-iodo-1H-pyrazole

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   ДругоеThe reaction mixture was partitioned between water and ethyl acetate
2. 2
   ЭкстракцияThe aqueous layer was extracted with additional ethyl acetate twice
3. 3
   ПромывкаThe combined organic layers were washed three times with water
4. 4
   Промывкаwashed with brine
5. 5
   Сушкаdried over MgSO4
6. 6
   Фильтрацияfiltered
7. 7
   Концентрированиеconcentrated
8. 8
   ДругоеThe residue was purified by flash column chromatography on silica gel eluting with 10% ethyl acetate in hexanes

Методика

A mixture of 1-bromo-3-(bromomethyl)-adamantane (1.0 g) and 4-iodopyrazole (0.63 g) in N,N-dimethylformamide (10 mL) was cooled to 0° C. To this solution was added 60% sodium hydride (0.20 g). The solution was stirred at 65° C. overnight. The reaction mixture was partitioned between water and ethyl acetate. The aqueous layer was extracted with additional ethyl acetate twice. The combined organic layers were washed three times with water, washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography on silica gel eluting with 10% ethyl acetate in hexanes to provide the title compound.

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