1,3-Propanediol → HCID 17984761, compound

Participants

Reaction Steps

A mixture of 3,6-dibromo-pyridazine (8.45 g, 35.5 mmol), palladacycle (0.66 g, 0.71 mmol), palladium acetate (0.16 g, 0.71 mmol), tri-tert-butylphosphine (0.35 ml, 1.42 mmol), aqueous potassium carbonate (2 M, 107 mmol), 1,3-propanediol (7.7 ml, 107 mmol) and 1,4-dioxane (100 ml) was stirred at reflux for 1 hour. 3-Thienyl boronic acid (5.0 g, 39.0 mmol) was added and the mixture was stirred at reflux for 7 days. Aqueous sodium hydroxide (50 ml, 1M) was added and the mixture was extracted with ethyl acetate (2×100 ml). Chromatography on silica gel with ethyl acetate:petroleum (1:3) as solvent gave the title compound. Yield 1.5 g (18%).

Provenance & Evidence