3-Bromopyridine → HCID 58188946, compound

Participants

Reaction Conditions

Reaction Steps

Into a 40 mL septum-cap vial were added sodium tert-butoxide (68 mg, 0.71 mmol), 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl (28 mg, 0.07 mmol), and Pd2(dba)3 (0.03 mmol). The vial was sealed and evacuated/purged 5× with nitrogen. A solution of 6-((S)-3-benzyl-piperazin-1-yl)-1-cyclobutyl-3-ethyl-1H-indazole (185 mg, 0.49 mmol) and 3-bromopyridine (158 mg, 1.02 mmol) in 3 mL of toluene was added, and the reaction mixture was heated at 100° C. for 15 h. The reaction mixture was cooled, filtered, concentrated, and purified by silica gel flash chromatography with a 0-100% EtOAc/Hexanes gradient to afford the title compound as a tan solid (30 mg, 13%). LC/MS (Method B) 3.10 min, [M+1]+ 452.

Provenance & Evidence