Sodium Carbonate → Ethyl 1-(6-{2-[(2,4-dimethylbenzyl)oxy]-3-methylphenyl}pyridin-2-yl)-5-(trifluoromethyl)-1H-pyrazole-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

A vial was charged with the product from Example 15 Step B (40 mg, 0.064 mmol), trimethyl boroxine (49 mg, 50 wt. %, 0.193 mmol), and 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (5.3 mg, 0.006 mmol). Sodium carbonate (0.161 mL, 1.0 M aqueous, 0.161 mmol) and THF (0.25 mL) were added, and the resulting suspension was degassed by a nitrogen sparge. The vial was then capped and placed in a pre-heated (65° C.) oil bath. After 18 h, the reaction mixture was allowed to cool to ambient temperature, then was poured into water. The aqueous phase was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by flash chromatography on silica gel (0 to 20% EtOAc in hexanes, then 20 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 510.8 [M+H]+.

Provenance & Evidence