Boron tribromide → 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylic acid

Participants

Reaction Steps

BBr3 (5 eq, 1 M sol. in CH2Cl2) was added to a solution of methyl 14-cyclohexyl-6-[(1-methyl-1H-pyrazol-4-yl)methyl]-5,6,7,8-tetrahydroindolo[2,1-a][2,5]benzodiazocine-11-carboxylate in CH2Cl2 (0.06 M), and the mixture stirred at RT for 40 mins. The volatiles were removed in vacuo. The crude was then purified by prep RP-HPLC (stationary phase: column Waters XTERRA prep. C18, 5 um, 19×150 mm. Mobile phase: MeCN/H2O buffered with 0.1% TFA). Fractions containing the pure compound were combined and freeze dried to afford the title compound as a white powder in a 7% yield (over two steps).

Provenance & Evidence