Реакция #42575

Уравнение реакции

3-Iodo-5-(methoxycarbonyl)benzoic acid

diisopropylethylamine

HATU

N-methylbutylamine

→

title compound

Methyl 3-{[butyl(methyl)amino]carbonyl}-5-iodobenzoate

Растворители

DMF

Условия реакции

Обработка

1. 1
   ДругоеThe reaction is partitioned between ethyl acetate and water
2. 2
   ПромывкаThe organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride
3. 3
   Сушкаdried (sodium sulfate)
4. 4
   Фильтрацияfiltered
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   ДругоеPurification by flash column chromatography (silica, 40% ethyl acetate/hexane)

Методика

3-Iodo-5-(methoxycarbonyl)benzoic acid (1 g, 3.3 mmol) is dissolved in DMF (10 mL), and diisopropylethylamine (1.7 mL, 9.8 mmol), HATU (1.5 g, 3.9 mmol), and N-methylbutylamine (581 μL, 4.9 mmol) are added. The reaction stirred at room temperature 2 h. The reaction is partitioned between ethyl acetate and water. The organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 40% ethyl acetate/hexane) provides the title compound. ESI MS m/z 376.1 [M+H]+.

Источник