Boron tribromide → HCID 136387753, compound

Participants

Reaction Steps

To 4-[2-methoxy-5-(trifluoromethyl)phenyl]pyridin-2-amine (Preparation 16, 2.8 g, 0.01 mmol) in dichloromethane (5 mL) at 0° C. was added drop-wise a 1.0 M solution of boron tribromide in dichloromethane (31.3 mL, 31.3 mmol). After stirring for 20 hours at ambient temperature, the reaction mixture was quenched with water and saturated aqueous sodium bicarbonate until basic. The aqueous phase was extracted with 15% isopropyl alcohol in chloroform (×3). The combined organic phase was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (0% to 10% methanol in chloroform gradient elution) and concentrated in vacuo to afford the title compound as a yellow solid (1.33 g).

Provenance & Evidence