Reaktion #91080

Reaktionsgleichung

2-iodo-4-methoxyaniline

ethyl-2-(2-oxocyclopentyl)acetate

tetraethyl orthosilicate

pyridine p-toluenesulfonate

DIPEA

→

title compound

Ethyl 2-(7-Methoxy-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetate

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto cool to 100° C.
2. 2
   workup.STIRRINGThe resulting mixture was stirred at 120° C. for 22 h under N2
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   Filtrationfiltered through a plug of silica
5. 5
   Sonstigethe solvent was evaporated under reduced pressure
6. 6
   SonstigeThe residue was purified by silica gel column chromatography

Vorschrift

To a solution of 2-iodo-4-methoxyaniline (20.0 g, 80 mmol), ethyl-2-(2-oxocyclopentyl)acetate (20.5 g, 120 mmol, 1.5 eq) and tetraethyl orthosilicate (21.7 g, 104 mmol, 1.3 eq) in anhydrous DMF (100 mL), was added pyridine p-toluenesulfonate (0.807 g, 3.21 mmol, 0.04 eq). The dark brown solution was stirred at 135° C. for 5 h under N2, allowed to cool to 100° C. and then added DIPEA (31.1 g, 241 mmol, 3 eq) followed by Pd(OAc)2 (0.541 g, 2.41 mmol, 0.03 eq). The resulting mixture was stirred at 120° C. for 22 h under N2, concentrated under reduced pressure. The residue was taken up in DCM, filtered through a plug of silica and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound. LCMS m/z 274.4 [M+H]+.

Quelle