Potassium Carbonate → 3-cyclopentyl-2-[4-(1H-indol-4-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of 1H-indol-4-ol (3.5 g, 26.6 mmol) in N,N-dimethylformamide (40 mL) was treated with potassium carbonate (5.4 g, 39 mmol) and 3-cyclopentyl-2-(4-iodo-6-oxo-6H-pyridazin-1-yl)-propionic acid methyl ester (Intermediate 73 step 2.10 g, 26.6 mmol). The resulting reaction mixture was heated to 120° C. for 2 h. At this time, the reaction was cooled to 25° C. and then concentrated in vacuo. The residue was partitioned between water and methylene chloride. The aqueous phase was back extracted with methylene chloride. The combined organics was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Chromatography afforded 3-cyclopentyl-2-[4-(1H-indol-4-yloxy)-6-oxo-6H-pyridazin-1-yl]-propionic acid methyl ester as a light oil (6.1 g, 60%).

Provenance & Evidence