Piperazine → HCID 57678298, compound

Participants

Reaction Conditions

Reaction Steps

4-tert-butyl-N-(2,6-dibromophenyl)benzenecarbothioamide prepared as in Example 19 (0.200 g, 0.468 mmol) was dissolved in dioxane (4 mL) and treated with Pd2 dba3 (4.3 mg, 0.0468 mmol), o-biphenyl(tBu)2P (15.4 mg, 0.0515 mmol) and Cs2CO3 (0.229 g, 0.702 mmol). The mixture was heated to 80° C. for 2 h until the starting material was consumed and cooled. To the reaction mixture was then added toluene (2 mL), Pd2 dba3 (4.3 mg, 0.0468 mmol), o-biphenyl(tBu)2P (15.4 mg, 0.0515 mmol), sodium tert-butoxide (0.090 g, 0.936 mmol) and piperazine (0.403 g, 4.68 mmol). The mixture was heated at 80° C. for 1 h and filtered through celite. The filtrate was diluted with dichloromethane, washed with water and saturated sodium chloride, and concentrated. The crude material was purified by reverse-phase HPLC to yield 69.5 mg (42%) of the product. MS (ES) m/z 352.1; HPLC Method B, purity 100% at 210-370 nm, 9.8 min.; 99.4% at 310 nm, 9.8 min.; HRMS: calcd for C21H25N3S+H+, 352.18419; found (ESI, [M+H]+), 352.1841.

Provenance & Evidence