Boron tribromide → HCID 59548014, compound

Participants

Reaction Steps

To a solution of 3-methyl-N-(1-{[4-(methyloxy)-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-4-pyridinecarboxamide (for a preparation see Example 175)(50 mg, 0.128 mmol) in dichloromethane (1 mL) was added slowly 1.0 M boron tribromide in DCM (0.26 mL, 0.260 mmol). The resulting colourless solution was stirred under nitrogen for 2 days. The reaction mixture ran dry, so further amounts of dichloromethane (1 ml) and 1.0 M boron tribromide in DCM (0.26 mL, 0.260 mmol) were added. The resulting white suspension was stirred at ambient temperature under nitrogen overnight. A further amount of 1.0 M boron tribromide in DCM (0.26 ml, 0.26 mmol) was added and stirred for a further 4 h. The solvent was removed in vacuo and the residue dissolved in 1:1 MeOH:DMSO (1 ml) and purified by MDAP on an Xbridge column using Acetonitrile-Water with an ammonium carbonate modifier (Method E). The solvent was evaporated in vacuo to give the title compound as a white solid (11 mg); LCMS (System 8) MH+=376, tRET=2.13 min.

Provenance & Evidence