tert-Butyl bromoacetate → HCID 59540602, compound

Participants

Reaction Steps

To a solution of 2,2-Dimethyl-1-[2-(3-piperazin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (0.233 g, 0.473 mmol) in 2 mL of dimethyl formamide was added 0.074 mL of diisopropylethylamine (0.055 g, 0.425 mmol) and 0.629 mL of tert-butyl bromoacetate (0.083 g, 0.425 mmol). The reaction was stirred at room temperature overnight before quenching with water and extracting with dichloromethane. The combined organics were washed with water, dried over MgSO4, filtered and concentrated in vacuo. Silica gel chromatography (10→60% EtOAc/hexanes over 30 minutes) afforded 0.1582 g (61% yield) of (4-{3-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-acetic acid tert-butyl ester as a yellow oil. MS (E/I): 608 (M+H).

Provenance & Evidence