Sodium Carbonate → HCID 57671358, compound

Participants

Reaction Conditions

Reaction Steps

Bring a mixture of trifluoro-methanesulfonic acid 3,5-dichloro-4-[(R)-2-oxo-1-(1-trifluoromethanesulfonyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-pyrrolidin-3-ylmethyl]phenyl ester and trifluoro-methanesulfonic acid 3,5-dichloro-4-[(R)-2-oxo-1-(2-trifluoromethanesulfonyl-4,5,6,7-tetrahydro-2H-indazol-4-yl)-pyrrolidin-3-ylmethyl]-phenyl ester (0.5 g, 0.78 mmol), 4-trifluoromethylphenylboronic acid (0.18 g, 0.93 mmol), sodium carbonate (0.25 g, 2.3 mmol) in THF (15 mL) and water (5 mL) to 60° C. To the mixture at 60° C., add Pd(PPh3)4 (0.04 g, 0.03 mmol). Raise the reaction temperature to 80° C. and stir the reaction for 1 hour. Cool the reaction, dilute with ethyl acetate, and wash with water and brine. Dry the organic layer (Na2SO4) and remove the solvent in vacuo to afford crude product (0.48 g). Dissolve in THF (5 mL) and stir in LiOH (2 N, 3 mL) at room temperature for 1.5 hour. Quench the reaction with HCl (1N, 8 mL), dilute with ethyl acetate, and wash with water. Dry the organic layer (Na2SO4), remove the solvent in vacuo to afford crude product, and then purify on silica gel column with 100% dichloromethane to 10% methanol in dichloromethane to afford 0.35 g of the title product. MS (m/z): 508 (M+).

Provenance & Evidence