1,3-Propanediol → HCID 131728754, compound

Participants

Reaction Steps

A mixture of 8-(6-iodo-pyridazin-3-yl)-10-methyl-8,10-diaza -bicyclo[4.3.1]-decane (1.5 g, 4.19 mmol), 3-thiopheneboronic acid (1.62 g, 12.56 mmol), potassium carbonate (1.74 g, 12.56 mmol), palladacycle (78 mg, 0.084 mmol), Pd(PPh3)4 (97 mg, 0.084 mmol), bis(tri-t-butylphosphine)palladium(0) (43 mg, 0.084 mmol), 1,3-propandiol (0.93 g, 12.6 mmol), DME (60 ml) and water (30 ml) was stirred at reflux for 40 h. Aqueous sodium hydroxide (40 ml, 1 M) was added followed by evaporation of the dioxane and extraction with chloroform (3×40 ml). Chromatography on silica gel with dichloromethane, 10% methanol and 1% aqueous ammonia as solvent gave the title compound as an oil. Yield 0.68 g, 52%. The corresponding salt was obtained by addition of a diethyl ether and methanol mixture (9:1) saturated with fumaric acid. LC-ESI -HRMS of [M+H]+ shows 315.1642 Da. Calc. 315.164342 Da, dev. −0.5 ppm

Provenance & Evidence