Morpholine → HCID 16048985, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(4-bromophenyl)-6-cyclobutyl-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Example 35) (80 mg, 0.23 mmol), morpholine (40 μl, 0.46 mmol), cesium carbonate (115 mg, 0.35 mmol), tris(dibenzylideneacetone)dipalladium(0) (10 mg, 0.01 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) (20 mg, 0.035 mmol) in dioxane (2 ml) was heated in the microwave (normal absorption) at 100° C. for 2 hours. The same amounts again of morpholine, cesium carbonate, tris(dibenzylideneacetone)dipalladium(0) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphane) were added and the mixture heated in the microwave at 150° C. for 2 hours. The reaction mixture was purified by SCX cartridge, followed by Mass Directed Autopreparation and column chromatography on silica gel, eluting with a mixture of 2M ammonia in methanol/dichloromethane (0-5%) to afford the title compound (E39). MS (ES+) m/e 353 [M+H]+.

Provenance & Evidence