Reaktion #339523

Reaktionsgleichung

3-methoxypropyne

5-bromo-3-iodo-1-methyl-1H-indazole

→

title compound

5-Bromo-3-(3-methoxyprop-1-ynyl)-1-methyl-1H-indazole

Lösungsmittel

N,N-dimethylformamide

water

triethylamine

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe reaction mixture is cooled to room temperature
2. 2
   Extraktionextracted with ethyl acetate (4×)
3. 3
   TrocknenThe combined organic phases are dried over sodium sulphate
4. 4
   Einengenconcentrated by evaporation

Vorschrift

A solution of 81.67 g of 5-bromo-3-iodo-1-methyl-1H-indazole in 750 ml of N,N-dimethylformamide and 335 ml of triethylamine is admixed at room temperature under argon with 25 ml of 3-methoxypropyne, 5.5 g of copper(I) iodide and 10 g of bis(triphenylphosphine)palladium(II) chloride, and subsequently heated to 60° C. After 1 hour, the reaction mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate (4×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow solid from the residue by means of flash chromatography (SiO2 60F). Rf=0.67 (2:1 EtOAc-heptane). Rt=4.42 (gradient I).

Quelle