Réaction #42579

Équation de réaction

3-Iodo-5-(methoxycarbonyl)benzoic acid

diisopropylethylamine

HATU

N-ethylpropylamine

→

title compound

Methyl 3-{[ethyl(propyl)amino]carbonyl}-5-iodobenzoate

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe reaction is partitioned between ethyl acetate and water
2. 2
   LavageThe organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride
3. 3
   Séchagedried (sodium sulfate)
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   AutrePurification by flash column chromatography (silica, 40% ethyl acetate/hexane)

Mode opératoire

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-ethylpropylamine (572 μL, 4.9 mmol) are added. The reaction stirred at room temperature 16 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]+.

Source