Reaktion #1018936

Reaktionsgleichung

(S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate

4-chlorophenylboronic acid

K2CO3

→

desired product

Ausbeute 73.0%

(S)-2-tert-Butoxy-2-(5-(4-chlorophenyl)-2,7-dimethylquinolin-6-yl)ethyl pivalate

Ausbeute 73.0%

Lösungsmittel

1,2-dimethoxyethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was flushed with nitrogen
2. 2
   Sonstigethe volatile component was removed in vacuo
3. 3
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate (100 mL)
4. 4
   Waschenwashed with NaHCO3 solution, water and brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe obtained residue was purified by flash chromatography

Vorschrift

Pd(PPh3)4 (69 mg, 0.06 mmol) was added to a mixture (S)-2-(5-bromo-2,7-dimethylquinolin-6-yl)-2-tert-butoxyethyl pivalate (5E) (325 mg, 0.75 mmol), 4-chlorophenylboronic acid (175 mg, 1.1 mmol), K2CO3 (1.3 mL 2 M in water, 2.6 mmol) in 1,2-dimethoxyethane (10 mL). The reaction mixture was flushed with nitrogen, heated at 110° C. for 30 min under microwave, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by flash chromatography to provide the desired product (256 mg, 73%). LCMS-ESI+ (m/z): 468.3, 469.3 (M+H)+.

Quelle