Reaktion #615152

Reaktionsgleichung

DMF

K2CO3

2-methoxy-8-[[(trifluoromethyl)sulfonyl]oxy]-5-quinoline carboxylic acid ethyl ester

→

(R)-1-amino-4-oxo-1,2-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-7-carboxylic acid ethyl ester

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGfurther stirred at 85° C. overnight
2. 2
   Extraktionextracted with ether
3. 3
   Trocknenlayer was dried over MgSO4
4. 4
   Einengenconcentrated to dryness
5. 5
   Sonstigepurified by CC (Hex/EA, 4:1)
6. 6
   Sonstigeaffording a yellow oil (5.40 g; 66% yield)

Vorschrift

A solution of vinylboronic anhydride pyridine complex (1:1; 3.81 g) in DMF (240 mL) was treated with tetrakis(triphenylphosphine)palladium(0) (731 mg) and stirred under nitrogen for 20 min. The reaction mixture was sequentially treated with K2CO3 (4.372 g) water (73 mL) and 2-methoxy-8-[[(trifluoromethyl)sulfonyl]oxy]-5-quinoline carboxylic acid ethyl ester (12.0 g; prepared in analogy to the corresponding n-butyl ester described in WO 2006/046552) and further stirred at 85° C. overnight. The reaction mixture was diluted with water and extracted with ether. The org. layer was dried over MgSO4, concentrated to dryness and purified by CC (Hex/EA, 4:1), affording a yellow oil (5.40 g; 66% yield).

Quelle