Reaktion #52417

Reaktionsgleichung

1-ethynyl-4-(1-methoxycyclopropyl)-benzene

4-(1-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-ylethynyl)-benzoic acid ethyl ester

Intermediate 61

4-(1-cyclopropyl-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-6-ylethynyl)-benzoic acid ethyl ester

ethyl-4-iodo benzoate

ethyl-4-iodo-benzoate

Reagent A

ethyl-4-iodo-benzoate

→

title compound

Ausbeute 90.0%

Ethyl 4-[4-(1-methoxycyclopropyl)-phenylethynyl]-benzoate

Ausbeute 90.0%

Lösungsmittel

triethyl amine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesparged with argon for 5 minutes

Vorschrift

Using General Procedure F; 1-ethynyl-4-(1-methoxycyclopropyl)-benzene (Intermediate 61, 100.0 mg, 0.47 mmol) and ethyl-4-iodo benzoate (Reagent A, 141.0 mg, 0.51 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (30.0 mg, 0.16 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (109 mg, 0.16 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-5% EtOAc—hexanes) afforded 135.0 mg (90%) of the title compound as an orange solid.

Quelle