Réaction #218087

Équation de réaction

potassium carbonate

3-ethoxy-4-hydroxy-benzaldehyde

hydrogen peroxide

3-methyl-butylamine

K2CO3

4-fluorobenzonitrile

→

title compound

4-{2-Ethoxy-4-[(3-methyl-butylamino)-methyl]-phenoxy}-benzamide

Ammonium bicarbonate

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   ExtractionAdd water and extract the aqueous layer with EtOAc
2. 2
   SéchageCombine organic layers and dry over Na2SO4
3. 3
   Autrepurify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85)
4. 4
   Autreto get
5. 5
   Autreto obtain
6. 6
   workup.ADDITIONa mixture of two compounds which
7. 7
   Autreis subject to hydrolysis
8. 8
   AutreThis mixture is purified by flash chromatography (EtOAc and CH2Cl2/MeOH 10%)

Mode opératoire

Dissolve 3-ethoxy-4-hydroxy-benzaldehyde (2.57 g, 15.45 mmol) in DMF (20 mL), add K2CO3 (2.33 g, 16.86 mmol) and 4-fluorobenzonitrile (1.70 g, 14.05 mmol), heat the mixture at 130° C. overnight. Add water and extract the aqueous layer with EtOAc. Combine organic layers and dry over Na2SO4. Eliminate the solvent and purify by flash chromatography on silica gel (eluent: EtOAc/hexane 15/85) to get a mixture of two compounds (1.45 g). This mixture (240 mg) is submitted to the reductive amination conditions described for compound 1 (step 3) using 3-methyl-butylamine to obtain a mixture of two compounds which is subject to hydrolysis using hydrogen peroxide and potassium carbonate in the conditions described elsewhere in this document. This mixture is purified by flash chromatography (EtOAc and CH2Cl2/MeOH 10%) and then the title compound is isolated after HPLC (Column: XTerraMSC18 (5 um, 19×100 mm). Isocratic mode: 55/45 Ammonium bicarbonate-pH 9-/Acetonitrile. Flow: 10 mL/min).

Source