Reacción #42579

Ecuación de reacción

3-Iodo-5-(methoxycarbonyl)benzoic acid

diisopropylethylamine

HATU

N-ethylpropylamine

→

title compound

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

Disolventes

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe reaction is partitioned between ethyl acetate and water
2. 2
   LavadoThe organic layer is washed with saturated sodium bicarbonate, and saturated sodium chloride
3. 3
   Secadodried (sodium sulfate)
4. 4
   Filtraciónfiltered
5. 5
   Concentraciónconcentrated under reduced pressure
6. 6
   OtroPurification by flash column chromatography (silica, 40% ethyl acetate/hexane)

Procedimiento

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]+.

Fuente