Potassium Carbonate → HCID 66900498, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-[4-(1H-indol-4-yloxy)-6-oxo-6H-pyridazin-1-yl]-4-methyl-pentanoic acid (1-methyl-1H-pyrazol-3-yl)-amide (34.0 mg, 0.0809 mmol) in N,N-dimethylformamide (1.0 mL) was treated with potassium carbonate (23.1 mg, 0.16 mmol) and toluene-4-sulfonic acid (S)-2,2-dimethyl-[1,3]dioxolan-4-yl ester (25.5 mg, 0.08 mmol). The resulting reaction mixture was heated at 90° C. overnight. At this time, the reaction mixture was allowed to cool to 25° C., concentrated in vacuo and was treated with a saturated aqueous ammonium chloride solution (2 drops). The reaction was then concentrated in vacuo onto silica gel. Silica gel column chromatography (AnaLogix 12 g, 1-5% methanol/methylene chloride) afforded 2-{4-[1-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-1H-indol-4-yloxy]-6-oxo-6H-pyridazin-1-yl}-4-methyl-pentanoic acid (1-methyl-1H-pyrazol-3-yl)-amide (9.0 mg, 21%) as a viscous brown oil.

Provenance & Evidence