Reaktion #1490708

Reaktionsgleichung

2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

(S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

sodium carbonate

→

(S)-methyl 2-(4-amino-3-nitrophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Ausbeute 75.1%

Lösungsmittel

ethylene glycol dimethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Einengenconcentrated under vacuum
2. 2
   Sonstigeto give a residue, which
3. 3
   Sonstigewas purified via silica gel chromatography (2% to 10% ethyl acetate in petroleum ether)

Vorschrift

To a solution of 2-nitro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.30 g, 4.92 mmol) in ethylene glycol dimethyl ether (100 mL) was added (S)-methyl 2-chloro-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate (1.0 g, 3.27 mmol), sodium carbonate (1.05 g, 9.91 mmol), and Pd(dppf)2Cl2 (0.12 g, 0.17 mmol). The resulting solution was stirred for 40 min at 90° C. under an N2 atmosphere, and then concentrated under vacuum to give a residue, which was purified via silica gel chromatography (2% to 10% ethyl acetate in petroleum ether) to afford (S)-methyl 2-(4-amino-3-nitrophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as an orange solid (1.0 g, 57%).

Quelle