1,3-Propanediol → Ammonia

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-[6-bromo-3-pyridazinyl]-(1S,4S)-5-tert-butoxycarbonyl-2,5-diazabicyclo-[2.2.1]-heptane (1.65 g, 4.64 mmol), thiophene-3-boronic acid (0.89 g, 6.97 mmol), palladium acetate (42 mg, 0.19 mmol), tri-tert-butylphosphine (38 mg, 0.19 mmol), palladacycle (87 mg, 0.10 mmol), aqueous potassium carbonate (13.9 mmol, 2M), 1,3-propanediol (1.0 ml, 13.9 mmol) and dioxane (50 ml) was stirred at 100° C. for eleven days. The mixture was evaporated, aqueous sodium hydroxide (50 ml, 1 M) was added and the mixture was extracted with ethyl acetate (3×50 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 0.68 g (41%).

Provenance & Evidence