Sodium t-butoxide → (S)-1'-(5-ethylpyrimidin-2-yl)-3-((6-fluoro-1,1-dioxido-2,3-dihydrobenzo[b]thiophen-5-yl)amino)-[1,4'-bipiperidin]-2-one

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 5-bromo-6-fluoro-2,3-dihydrobenzo[b]thiophene 1,1-dioxide (0.070 g, 0.26 mmol), (S)-3-amino-1′-(5-ethylpyrimidin-2-yl)-[1,4′-bipiperidin]-2-one (Steps A-C, 0.05 g, 0.16 mmol), Pd2 dba3 (0.0075 g, 0.0082 mmol), Binap-rac (0.0010 g, 0.0016 mmol), sodium t-butoxide (0.033 g, 0.35 mmol), and degassed toluene (3 mL). The reaction was stirred at 90° C. for 4 hours. The organic solvent was removed under reduced pressure. The residue was purified using silica gel column chromatography with 50-100% ethyl acetate, followed by preparative TLC using 2% methanol in ethyl acetate to provide (S)-1′-(5-ethylpyrimidin-2-yl)-3-((6-fluoro-1,1-dioxido-2,3-dihydrobenzo[b]thiophen-5-yl)amino)-[1,4′-bipiperidin]-2-one (0.025 g, 0.051 mmol, 31% yield) as off white solid. Mass spectrum (apci) m/z=488.3 (M+H).

Provenance & Evidence