tert-Butyldimethylsilyl trifluoromethanesulphonate → 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methyl-N-(2-methyl-4-(methylsulfonyl)butan-2-yl)quinoxalin-2-amine

Participants

Reaction Steps

A solution of 1-(2-methyl-3-((2-methyl-4-(methylsulfonyl)butan-2-yl)amino)quinoxalin-5-yl)ethanone (338c, 0.51 g, 1.46 mmol), tert-butyldimethylsilyl trifluoromethanesulfonate (0.50 mL, 2.20 mmol), and TEA (0.61 mL, 4.40 mmol) in DCM (14.68 mL) was stirred at 0° C. for 30 min when silyl enol ether was observed via lcms. The reaction mixture was diluted with DCM (150 mL), added to a separatory funnel, and washed with saturated aq. NaHCO3 (75 mL) before the organic layer was separated, dried over Na2SO4, and concentrated to give 8-(1-((tert-butyldimethylsilyl)oxy)vinyl)-3-methyl-N-(2-methyl-4-(methylsulfonyl)butan-2-yl)quinoxalin-2-amine (338d) as a yellow oil. MS (ESI, pos. ion) m/z: 464.2 (M+1).

Provenance & Evidence