Boron tribromide → HCID 67355200, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave vial was added 4-[4-bromo-2-(methyloxy)phenyl]-5-{[(3S)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-one (132 mg, 0.313 mmol) and the solid was purged with nitrogen. Dichloromethane (1.5 mL) was added to the solid and was cooled to 0° C. Boron tribromide (2.037 mL, 2.037 mmol, 1M in dichloromethane) was added to the cooled solution and allowed to warm to room temperature. Analysis by LCMS indicated the presence of desired product and starting material. The solution was re-cooled to 0° C. and slowly treated with another portion of boron tribromide (2.037 mL, 2.037 mmol, 1M in dichloromethane). Analysis by LCMS indicated the consumption of starting material and presence of desired product. The solution was concentrated, dissolved in 2 mL dimethylsulfoxide, and purified by reverse phase HPLC (10-90% acetonitrile/water with 0.1% TFA). The desired fractions were collected and added to a separatory funnel containing ethyl acetate. The aqueous phase was adjusted to pH˜6 with 1N aq HCl. The aqueous phase was extracted with ethyl acetate (3×), and the combined organics were washed with brine, dried over sodium sulfate, and concentrated in vacuo to afford the title product as a white solid (95 mg, 75%). MS(ES)+ m/e 407.1, 409.0 M+H]+.

Provenance & Evidence