Cesium carbonate → HCID 90203799, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 5-Bromo-4-(2,2,2-trifluoro-ethoxy)-pyridine-2-carboxylic acid [1-(N-hydroxycarbamimidoyl)-1,3,3-trimethyl-butyl]-amide (Example 97c, 0.175 g, 365 μmol) in toluene (2 ml) under an argon atmosphere was added potassium cyclopropytrifluoroborate (108 mg, 730 μmol), palladium (II) acetate (4.1 mg, 18.3 μmol), butyldi-1-adamantylphosphine (13.1 mg, 36.5 μmol) and cesium carbonate (243 μl, 730 μmol). The reaction was stirred at 125° C. for 18 hours. The reaction was filtered through a pad of celite. The filtrate was diluted with ethylacetate and was extracted with an 1.0M aqueous solution of sodium bicarbonate. The organic phase was dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a heptane/ethylacetate gradient to yield the title compound (154 mg, 96%) as a light yellow oil. MS (ESI, m/z): 441.7 (M+H+).

Provenance & Evidence