1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 58115030, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (250 mg, 0.76 mmol), 2-propargyl-1-methyl-piperidine (105 mg, 0.76 mmol), copper iodide (15 mg, 0.076 mmol), dichlorobis-(triphenylphosphine)palladium (II) (11 mg, 0.02 mmol) and DBU (0.34 mL, 2.28 mmol) in dry dimethyl acetamide (3 mL). The mixture was vacuum degassed and heated to 120° C. and stirred for 10 hours. The mixture was cooled to ambient and quenched via the addition of water (45 ml) and ethyl acetate (45 ml). The material was shaken in a separatory funnel, and the ethyl acetate phase was collected. The aqueous phases were back extracted with ethyl acetate (2×40 ml), the organics combined, dried (MgSO4), filtered and stripped. The remainder was purified by preparative TLC using 15% ethyl acetate in hexanes as eluant. The plates were re-developed consecutively with 40% and then 60% ethyl acetate in hexanes. The product band was collected to provide 185 mg of (+/−)-2-[3-(2-methyl-piperidin-1-yl)-prop-1-ynyl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine as a golden yellow oil. MS (M+H)+=385

Provenance & Evidence