Reacción #42343

Ecuación de reacción

N-methylpropylamine

3-iodo-5-(methoxycarbonyl)benzoic acid

diisopropylethylamine

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate

→

title compound

Methyl 3-iodo-5-{[methyl(propyl)amino]carbonyl}benzoate

Disolventes

ethyl acetate

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water, saturated sodium bicarbonate, and brine
2. 2
   SecadoThe organic layer is dried over sodium sulfate
3. 3
   Filtraciónfiltered
4. 4
   Concentraciónconcentrated under reduced pressure

Procedimiento

To 3-iodo-5-(methoxycarbonyl)benzoic acid (1.0 g, 3.3 mmol), prepared as in Example SP-281, step 1, and diisopropylethylamine (1.7 mL, 9.8 mmol) in DMF (10 mL) is added O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 1.5 g, 3.9 mmol) then N-methylpropylamine (503 μL, 4.9 mmol). The solution is stirred at room temperature 2 h. The solution is diluted in ethyl acetate and washed with water, saturated sodium bicarbonate, and brine. The organic layer is dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound in crude form. This material is purified by flash chromatography (40% ethyl acetate/hexane) to give the purified title compound. MS (ESI) [M+H+]=362.4.

Fuente