Potassium Phosphate, Tribasic → HCID 46944993, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of N-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-2-chlorobenzamide (for a preparation see Example 95)(30 mg, 0.059 mmol) was added potassium phosphate tribasic (38 mg, 0.179 mmol, Aldrich), tricyclohexyl phosphine (5 mg, 0.018 mmol, Aldrich), cyclopropyl boronic acid (16 mg, 0.186 mmol, Fluorochem) in toluene (2 ml). Water (0.1 ml) was added followed by palladium (II) acetate (4 mg, 0.018 mmol, ABCR). The resulting yellow suspension was heated to 100° C. and stirred under nitrogen overnight. The reaction mixture was partitioned between DCM (10 ml) and water (10 ml). The phases were separated using a hydrophobic frit and the aqueous layer was washed with DCM (10 ml). The organic layers were combined and the solvent removed in vacuo. The residue was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by MDAP on Sunfire C18 column (Method B) using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a yellow gum (6 mg); LCMS: (System 4) MH+=420, tRET=3.22 min.

Provenance & Evidence