Reaktion #547279

Reaktionsgleichung

dichloromethane

5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester

5-Methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester

1-difluoromethoxy-4-iodo-benzene

cesium carbonate

→

compound 152

Ausbeute 60.4%

4-(4′-difluoromethoxy-biphenyl-4-ylsulphanylmethyl)-5-methyl-furan-2-carboxylic acid methyl ester

Ausbeute 60.4%

Lösungsmittel

1,4-dioxan

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling
2. 2
   Einengenthe mixture was concentrated
3. 3
   Sonstigethe residue was partitioned between ethyl acetate and water
4. 4
   WaschenThe organic phase was washed with brine
5. 5
   Sonstigedried
6. 6
   SonstigeAfter evaporation of the solvent
7. 7
   Sonstigethe residue was purified by flash chromatography

Vorschrift

[1,1′-Bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (1:1) (12.8 mg) was added to a degassed mixture of 5-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylsulphanylmethyl]-furan-2-carboxylic acid methyl ester (151) (200 mg, 0.516 mmoles), 1-difluoromethoxy-4-iodo-benzene (153 mg, 0.568 mmoles) and 2M aqueous cesium carbonate (4.12 ml) in 1,4-dioxan (15 ml). The mixture was placed under an argon atmosphere and was heated at 100° C. for 20 hours. After cooling, the mixture was concentrated and the residue was partitioned between ethyl acetate and water, and the mixture adjusted to pH=2 with 1M aqueous hydrochloric acid. The organic phase was washed with brine and dried. After evaporation of the solvent, the residue was purified by flash chromatography, using heptane/ethyl acetate 9:1v/v as eluent, to afford compound 152(126 mg) as a white solid. LC/MS System A; Rt=4.17 mins.

Quelle