Cesium carbonate → 6-(Benzenesulphonylmethyl)-3-(furan-2-yl)-2-methoxybenzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(benzenesulphonylmethyl)-3-bromo-2-methoxybenzoic acid (Example 7, 0.1 g), 2-furylboronic acid (0.031 g), tri-tert-butylphosphinium tetrafluoroborate (0.0074 g), cesium carbonate (0.253 g) and tris-(dibenzylideneacetone)dipalladium (0.012 g) in dioxane (3 ml) and water (0.4 ml) was sealed in a vial under nitrogen and heated at 80° C. for 2 hours. After cooling, the mixture was diluted with t-butyl methyl ether, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified twice by preparative HPLC (C18), eluting with a mixture of methanol and water containing 0.1% formic acid with a gradient of 25-98% to give 6-(benzenesulphonylmethyl)-3-(furan-2-yl)-2-methoxybenzoic acid (0.032 g) as a white solid.

Provenance & Evidence