Lithium Hydroxide → HCID 70818201, compound

Participants

Reaction Steps

To a solution of ethyl (2R)-2-methyl-2-(methylsulfonyl)-4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]butanoate (0.2 g, 0.5 mmol) in MeOH (2.5 mL) in a microwave reactor vial was added 2-(4-bromophenyl)-1,3-oxazole (0.118 g, 0.525 mmol, 1.05 eq), potassium carbonate (0.214 g, 1.5 mmol, 3 eq), and palladium tetrakis (0.117 g, 0.1 mmol, 0.2 eq). The reaction mixture was irradiated at 120° C. in a microwave reactor for five minutes. The vial was allowed to cool to RT, and a solution of lithium hydroxide (0.036 g, 1.5 mmol, 3 eq) in water (2 mL) was added. The reaction mixture was allowed to stir at room temperature for one hour. The mixture was then washed with ethyl acetate (100 mL) and 1M sodium hydroxide (50 mL). The aqueous layer was separated and acidified to pH 1 with 6M HCl. The aqueous layer was extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated to give (2R)-2-methyl-2-(methylsulfonyl)-4-{4-[4-(1,3-oxazol-2-yl)phenyl]-1H-pyrazol-1-yl}butanoic acid (0.125 g, 64% yield) as a white solid. LC-MS M+H+390.1.

Provenance & Evidence