Sodium Carbonate → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

Pd(PPh3)4 (4.6 mg, 0.004 mmol) was added to a mixture (S)-2-tert-butoxy-2-(5-(4-chlorophenyl)-7-methyl-2-(trifluoromethylsulfonyloxy)quinolin-6-yl)ethyl pivalate (compound of Example 26) (25 mg, 0.04 mmol), 4-chlorophenylboronic acid (13 mg, 0.08 mmol), Na2CO3 (0.14 mL 1 M in water, 0.14 mmol) in 1,2-dimethoxyethane (2 mL). The reaction mixture was flushed with nitrogen, heated at 90° C. for 16 hours, and then the volatile component was removed in vacuo. The residue was dissolved in ethyl acetate (100 mL), washed with NaHCO3 solution, water and brine, dried over Na2SO4, filtered and concentrated in vacuo. The obtained residue was purified by HPLC to provide the desired product as a TFA salt (15 mg, 55%). LCMS-ESI+ (m/z): 564.3, 566.3, 568.3 (M+H)+.

Provenance & Evidence