Reaktion #995741

Reaktionsgleichung

ethyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate

phenylboronic acid

Sodium carbonate

phenyl boronic acid

→

desired product

Ethyl 2-(4-hydroxy-1-methyl-2-oxo-6-phenyl-1,2-dihydroquinoline-3-carboxamido)acetate

Lösungsmittel

N,N-Dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe reaction mixture was concentrated on a roto-evaporator
2. 2
   Extraktionextracted with EtOAc
3. 3
   WaschenThis product was then washed with water and brine
4. 4
   Trocknendried with MgSO4
5. 5
   Einengenconcentrated on a roto-evaporator
6. 6
   Sonstigeto give the crude product as a red-orange oil
7. 7
   SonstigeThe crude product was purified by silica flash chromatography (10-75% EtOAc:Hex step gradient)

Vorschrift

A solution of ethyl 2-(4-hydroxy-6-iodo-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (200 mg, 465 μmol), phenylboronic acid (85 mg, 697 μmol), 2M Sodium carbonate (0.7 ml, 1395 μmol), Tetrakis(triphenylphosphine) palladium(0) (5 mg, 5 μmol) and N,N-Dimethylformamide (10 ml) was stirred at 100° C. After 8 hrs, an additional equivalent of the phenyl boronic acid was added, and the mixture was stirred for 15 hrs. The reaction mixture was concentrated on a roto-evaporator and extracted with EtOAc. This product was then washed with water and brine, then dried with MgSO4 and concentrated on a roto-evaporator to give the crude product as a red-orange oil. The crude product was purified by silica flash chromatography (10-75% EtOAc:Hex step gradient) to give the desired product as a white solid. Yield=120 mg. In some cases, ester hydrolysis was observed and the carboxylic acid was isolated.

Quelle