Реакция #8249

Уравнение реакции

sodium bicarbonate

Pyridine

5-Amino-2-(2-methylimidazol-1-yl)fluorobenzene

benzyl chloroformate

→

title product

Выход 93.5%

5-Benzyloxycarbonylamino-2-(2-methylimidazol-1-yl)fluorobenzene

Выход 93.5%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   Температураcooled to −5°
2. 2
   Другоеthe organic layer separated
3. 3
   Экстракцияthe aqueous layer re-extracted with dichloromethane (2×300 ml)
4. 4
   Сушкаdried (magnesium sulfate)
5. 5
   ФильтрацияAfter filtration and evaporation
6. 6
   Другоеthe residue was recrystallised from toluene (400 ml)

Методика

5-Amino-2-(2-methylimidazol-1-yl)fluorobenzene (34.25 g, 0.179 M) was dissolved in dry dichloromethane (600 ml) under nitrogen, and cooled to −5°. Pyridine (17.7 g, 0.224 M) was added, followed by benzyl chloroformate (33.7 g, 0.197 M) over 20 minutes. The mixture was stirred and the temperature allowed to rise to ambient over 16 hours. Aqueous sodium bicarbonate (5%, 250 ml) was added, the organic layer separated, the aqueous layer re-extracted with dichloromethane (2×300 ml), and combined extracts dried (magnesium sulfate). After filtration and evaporation, the residue was recrystallised from toluene (400 ml) to give title product (54.5 g).

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