1,3-Propanediol → HCID 69413856, compound

Participants

Reaction Steps

A mixture of 2-[5-bromo-6-chloro-2-pyrazinyl]-(1S,4S)-5-tert-butoxycarbonyl-2,5-diazabicyclo-[2.2.1]-heptane (4.0 g, 10.3 mmol), 3-thiophene boronic acid, aqueous potassium carbonate (15.4 ml, 2 M), 1,3-propandiol (2.34 g, 30.8 mmol), palladacycle (96 mg, 0.10 mmol), tri-tert-butylphosphine (83 mg, 0.41 mmol), palladium acetate (46 mg, 0.20 mmol) and dioxane (40 ml) was stirred at reflux for 5 days. Aqueous sodium hydroxide (50 ml, 1 M) was added and the mixture was extracted with ethyl acetate (2×30 ml). Chromatography on silica gel with ethyl acetate and petroleum (1:1) gave the title compound as an oil. Yield 1.46 g (41%). This single step also includes 6-dechlorination.

Provenance & Evidence