N-bromobutanimide → HCID 86686742, compound

Participants

Reaction Steps

N-{1-[7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]ethyl}-2,2,5-trimethyl-1,3-dioxane-5-carboxamide (370 mg, 0.501 mmol) was dissolved in acetic acid (13 mL). and N-bromosuccinimide (104 mg, 0.585 mmol) was added in a single portion, and the reaction was stirred for 10 min before being quenched with 20% aq. Na2S2O3 (20 mL) and saturated aq. NaHCO3 (60 mL) and EtOAc (50 mL). Solid NaHCO3 was added until the pH was above 5. The layers were separated, and the aqueous was extracted with EtOAc (2×50 mL). The combined organics were washed with brine (50 mL), dried with MgSO4, filtered, and concentrated in vacuo to give N-{1-[7-(bis{[2-(trimethylsilyl)ethoxy]methyl}amino)-6-bromo-3-(6-fluoroquinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl]ethyl}-2,2,5-trimethyl-1,3-dioxane-5-carboxamide, which was used without further purification.

Provenance & Evidence