Reaktion #52418

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

methyl-(4-iodophenyl)-acetate

4-iodo phenyl acetic acid methyl ester

Reagent B

4-iodo phenyl acetic acid methyl ester

triethyl amine

→

title compound

Ausbeute 78.0%

Methyl{4-[4-(1-methoxycyclopropyl)-phenylethynyl]-phenyl}-acetate

Ausbeute 78.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigesparged with argon for 5 minutes

Vorschrift

Using General Procedure F; 1-ethynyl-4-(1-methoxycyclopropyl)-benzene (Intermediate 61, 120.0 mg, 0.56 mmol) and methyl-(4-iodophenyl)-acetate (Reagent B, 154.0 mg, 0.56 mmol) in triethyl amine (6 mL) was treated with copper(I)iodide (35.0 mg, 0.19 mmol) and sparged with argon for 5 minutes. Dichlorobis(triphenylphosphine)palladium(II) (130 mg, 0.19 mmol) was added and the reaction mixture was stirred overnight at room temperature. Column chromatography (2-8% EtOAc—hexanes) afforded 140.0 mg (78%) of the title compound as an orange solid.

Quelle