Cesium carbonate → methyl (4S,7S)-4-(5-(4-(6-bromoquinoxalin-2-yl)phenyl)-1H-imidazol-2-yl)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate

Participants

Reaction Conditions

Reaction Steps

In a 10 ml seal tube, methyl (4S,7S)-6,10-dioxo-4-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)octahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate (240 mg, 459 μmol) (Intermediate 3), 6-bromo-2-chloroquinoxaline (112 mg, 459 μmol) and Cs2CO3 (299 mg, 917 μmol) were combined with 1,4-dioxane (3.00 ml) and water (0.5 ml) to give a light brown solution. It was degassed for 10 min and tetrakis(triphenylphosphine)palladium (0) (53.0 mg, 45.9 μmol) was added. The reaction mixture was heated at 80° C. for 16 h. It was diluted with EtOAc (6 ml) and concentrated in vacuo. The residue was purified on a silica gel column (CH2Cl2, 2%, 3%, 5%, 8% and 10% MeOH/CH2Cl2) to afford methyl (4S,7S)-4-(5-(4-(6-bromoquinoxalin-2-yl)phenyl)-1H-imidazol-2-yl)-6,10-dioxooctahydro-1H-pyridazino[1,2-a][1,2]diazepin-7-ylcarbamate as a red solid (240 mg, 86.6%). ESI-LRMS m/e calcd for C28H26BrN7O4 [M+] 604. found 605 [M+H+].

Provenance & Evidence