Cesium carbonate → 4-(5,5-Dioxo-5H-5lambda6-dibenzothiophen-3-yl)-1,4-diazabicyclo[3.2.2]nonane

Participants

Reaction Conditions

Reaction Steps

A catalyst solution was prepared by mixing tris(dibenzylideneacetone)dipalladium (Pd2(dba)3; 15 mg, 0.016 mmol; Alfa) and racemic 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP; 21 mg, 0.033 mmol; Strem) in toluene (1 mL) and heating the mixture to 90° C. for 15 min. The solution was cooled, and then added to a mixture of 1,4-diazabicyclo[3.2.2]nonane (105 mg, 0.83 mmol; see J. Med. Chem. 1993, 36, 2311) and 3,7-dibromodibenzothiophene-5,5-dioxide (0.60 g, 1.60 mmol; see J. Med. Chem. 1978, 21, 1084), in toluene (3 mL). Cs2CO3 (1.04 g, 3.2 mmol; Aldrich) was then added, and the reaction mixture was flushed with nitrogen and heated to 80-85° C. overnight. After cooling to room temperature, the mixture was filtered through diatomaceous earth and purified by chromatography (35 g silica gel, 1-10% gradient of NH4OH-MeOH (1:10) in CH2Cl2) to afford the title compound (102 mg, 0.30 mmol, 36% yield): MS (DCI/NH3) m/z 341 (M+H)+.

Provenance & Evidence