Reaktion #57645

Reaktionsgleichung

3-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester

K2CO3

pyridine-4-boronic acid

1,2-dimethoxyethane

→

3-methyl-4-pyridin-4-yl-benzofuran-2-carboxylic acid tert-butyl ester

Ausbeute 74.2%

Lösungsmittel

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   Extraktionwas extracted with ethyl acetate
3. 3
   ExtraktionThe organic extract
4. 4
   Waschenwas washed with water
5. 5
   Trocknendried over sodium sulfate
6. 6
   SonstigeRemoval of solvent
7. 7
   Sonstigegave the crude product, which
8. 8
   Sonstigewas purified by column chromatography

Vorschrift

3-Methyl-4-trifluoromethanesulfonyloxy-benzofuran-2-carboxylic acid tert-butyl ester (258 mg, 0.68 mmol) was mixed with K2CO3 (207 mg, 2.2 eq), pyridine-4-boronic acid (110 mg, 1.3 eq), Pd(Ph3)4 (43 mg, 0.05 eq), 3 mL of 1,2-dimethoxyethane and 0.5 mL of water. The mixture was heated and stirred in an 85° C. oil bath for 5 h. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic extract was washed with water and dried over sodium sulfate. Removal of solvent gave the crude product, which was purified by column chromatography to give 156 mg of 3-methyl-4-pyridin-4-yl-benzofuran-2-carboxylic acid tert-butyl ester, obtained as white solid.

Quelle