Potassium Carbonate → HCID 59452210, compound

Participants

Reaction Steps

Palladium (II) acetate (1.5 mg, 5 μmol) was added to a mixture of 1-(2-fluoro-4-iodo-benzyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid ((R)-2,2-dimethyl-[1,3]-dioxolan-4-ylmethoxy)-amide (55 mg, 0.11 mmol), trimethylsilylacetylene (138 μl, 1.0 mmol) and triphenylphosphine (3 mg, 10 μmol) in piperidine (0.5 ml). The resultant mixture was heated at 150° C. under microwave irradiation for 10 seconds. The reaction mixture was diluted with ethyl acetate (35 ml) and washed sequentially with water (10 ml), then brine (10 ml). The organic layer was isolated, dried over magnesium sulphate and concentrated in vacuo to provide a residue. The residue was dissolved in methanol (5 ml) to which potassium carbonate (29 mg, 0.21 mmol) was added, and the resultant suspension was stirred at room temperature for 2 hours. The reaction mixture was filtered, concentrated in vacuo, and then partitioned between ethyl acetate (25 ml) and water (20 ml). The organic layer was isolated, dried over magnesium sulphate and concentrated in vacuo to provide a residue. Purification by flash chromatography (Si-SPE, dichloromethane:ethyl acetate, 100:0 to 70:30 to 40:60 to 0:100) afforded the title compound as a yellow solid (30 mg, 68%). LCMS (method B): RT=2.21 min, (M−H)−=422, (M+H)+=424.

Provenance & Evidence