Boron tribromide → HCID 22346418, compound

Participants

Reaction Steps

To a solution of 5-[[(dimethylamino)carbonyl](methyl)amino]-N-(4-fluorobenzyl)-8-methoxy-1,6-naphthyridine-7-carboxamide from step 2 in CH2Cl2 (1 mL) at −78 C was added boron tribromide (0.10 mL of a 1M solution in CH2Cl2, 0.01 mmol). The reaction was allowed to warm to room temperature and stirred an additional 16 hr. The solvent was evaporated in vacuo and the residue dissolved in MeOH (2 mL) and the solvent again evaporated in vacuo. The residue was dissolved in DMF (1 mL) and purified by reverse phase HPLC. (Vydak C18, Gradient elution with Water:Acetonitrile 95:5 to 5:95 with 0.1% TFA at 30 mL/min over 15 mins). Lyophilization of the pure fractions afforded the title compound as an off white solid.

Provenance & Evidence