Reaktion #91053

Reaktionsgleichung

4-fluoro-3,5-diisopropoxybenzoic acid

4-Fluoro-3,5-diisopropoxybenzoic acid

DIPEA

T3P

methyl 4-aminobenzoate

4-chloro-3-ethoxy-5-(pentan-3-yloxy)benzoic acid

→

methyl 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoate

Ausbeute 51.0%

Methyl 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoate

Ausbeute 51.0%

Lösungsmittel

EtOAc

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   Sonstigepurified by silica gel chromatography (4 g, 0-100% EtOAc in isohexane)

Vorschrift

A mixture of 4-fluoro-3,5-diisopropoxybenzoic acid (8) (54 mg, 0.21 mmol), DIPEA (110 μL, 0.632 mmol) and T3P (50% solution in EtOAc) (310 μL, 0.527 mmol) in EtOAc (1 mL) was stirred at RT for 10 min before a solution of methyl 4-aminobenzoate (9) (35 mg, 0.23 mmol) in EtOAc (1 mL) was added dropwise and the mixture was stirred at 40° C. for 20 h. The reaction mixture was adsorbed on to silica and purified by silica gel chromatography (4 g, 0-100% EtOAc in isohexane), then (4 g, 0-10% MeOH in DCM) to afford methyl 4-(4-fluoro-3,5-diisopropoxybenzamido)benzoate (10) (32 mg, 51% purity). The material was taken on in the subsequent reaction step without further purification.

Quelle