Reaktion #73232

Reaktionsgleichung

1-Benzothien-2-ylboronic acid

Potassium carbonate

toluene

ethanol

4-bromo-1-[2-(trimethylsilyl)-ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine

→

4-(1-benzothien-2-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]-pyridine

Ausbeute 87.6%

Lösungsmittel

water

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONthen was added
2. 2
   Sonstigethe reaction was degassed with nitrogen
3. 3
   Temperaturto cool to rt
4. 4
   Waschenwashed with water 2×, brine
5. 5
   Trocknendried over magnesium sulfate
6. 6
   Einengenconcentrated

Vorschrift

1-Benzothien-2-ylboronic acid (0.05 g, 0.0003 mol) and 4-bromo-1-[2-(trimethylsilyl)-ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine (0.10 g, 0.00031 mol) were combined in toluene (3.0 mL, 0.028 mol) and ethanol (1.0 mL, 0.017 mol). Potassium carbonate (0.085 g, 0.00062 mol) dissolved in water (1.0 mL) then was added and the reaction was degassed with nitrogen. Then tetrakis(triphenylphosphine)palladium(0) (0.05 g, 0.00004 mol) was added and the reaction was heated to 120° C. in a sealed tube in the microwave for 60 minutes. This was allowed to cool to rt, taken up in ethyl acetate and washed with water 2×, brine, dried over magnesium sulfate and concentrated to give 4-(1-benzothien-2-yl)-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]-pyridine (0.10 gm) as an oil, LC/MS (M+H)+ 381.

Quelle