Reaction #42343

Reaction equation

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

Solvents

ethyl acetate

DMF

Conditions

Workup

1. 1
   Washwashed with water, saturated sodium bicarbonate, and brine
2. 2
   DryingThe organic layer is dried over sodium sulfate
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated under reduced pressure

Procedure

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.

Source