Reaktion #1772602

Reaktionsgleichung

5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylo-pyranoside

4-(trifluoromethoxy)phenylboronic acid

cesium fluoride

→

expected product

Ausbeute 68.0%

5-(4-trifluoromethoxyphenyl)-3-pyridinyl 5-thio-β-D-xylopyranoside

Ausbeute 68.0%

Lösungsmittel

methanol

DME

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationIt is filtered
2. 2
   Einengenconcentrated under reduced pressure
3. 3
   SonstigeThe crude product is purified by chromatography on a silica column (eluent: dichloromethane/methanol 90/10; v/v)

Vorschrift

0.5 g (1.11 mM) of 5-bromo-3-pyridinyl 2,3,4-tri-O-acetyl-5-thio-β-D-xylo-pyranoside, 0.275 g (1.33 mM) of 4-(trifluoromethoxy)phenylboronic acid, 0.373 g (2.45 mM) of cesium fluoride and 0.24 g of tetrakis(triphenylphosphine)palladium catalyst grafted onto polystyrene resin are mixed in 3.5 ml of DME and 5 ml of methanol. The reaction mixture is heated at 110° C. for 20 minutes by microwaves. It is filtered and then concentrated under reduced pressure. The crude product is purified by chromatography on a silica column (eluent: dichloromethane/methanol 90/10; v/v) to give the expected product in the form of a white solid with a yield of 68%.

Quelle