1,8-Diazabicyclo(5.4.0)undec-7-ene → (2-ethanesulfonyl-ethyl)-methyl-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-3,4,8a-triaza-as-indacen-8-yl]-amine

Participants

Reaction Conditions

Reaction Steps

A flask was charged with 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (295 mg, 0.9 mmol), 4-propargyl-thiomorpholine-1,1-dioxide (commercial, 156 mg, 0.9 mmol), copper iodide (17 mg, 0.09 mmol), dichlorobis-(triphenylphosphine)palladium (II) (13 mg, 0.018 mmol) and DBU (0.4 mL, 2.7 mmol) in dry dimethyl acetamide (3 mL). The mixture was vacuum degassed and heated to 80° C. under argon. After 1.5 hours the material was warmed to 120° C. and stirred for 12 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 reparatory 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 45% ethyl acetate in hexanes as eluant to provide 232 mg of (2-ethanesulfonyl-ethyl)-methyl-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-3,4,8a-triaza-as-indacen-8-yl]-amine as a dark brown oil. MS (M+H)+=421.

Provenance & Evidence