Sodium t-butoxide → HCID 24906104, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (2R)-1-[(3-bromophenyl)sulfonyl]-4-[4-fluoro-2-(trifluoromethyl)phenyl]-2-methylpiperazine (8 g, 16.667 mmol), N-Me-piperazine (2.22 mL, 20 mmol), bis-t-Bu-biphenylphosphine (298.2 mg, 1.0 mmol), tBuONa (2.4 g, 25 mmol) and Pd2(dba)3 (305.2 mg, 0.333 mmol) was mixed and purged with N2. Anhydrous toluene (80 mL) was added and purged with N2 again. The resultant mixture was heated in an oil bath at 110° C. under N2 for 5 hours. After cooling, diluted with EtOAc (100 mL), filtered through a pad of Celite and washed with EtOAc (100 mL). The combined organic layer washed with aq. NaHCO3. The aqueous layer was back extracted with EtOAc (2×50 mL). The combined organic layer was dried over Na2SO4. The crude product was purified on SiO2 gel column eluted with 0-25% MeOH in EtOAc to give the desired product as a light yellow solid (6.5 g, 78%). HRMS: calcd for C23H28F4N4O2S+H+, 501.19418. found (ESI-FTMS, [M+H]1+), 501.1944.

Provenance & Evidence