Cesium carbonate → benzhydrylidene-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine

Participants

Reaction Conditions

Reaction Steps

2-Bromo-6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine (0.340 g, 0.993 mmol), benzhydrylideneamine (0.18 mL, 1.09 mmol), Cs2CO3 (648 mg, 1.99 mmol), Pd(OAc)2 (22 mg, 0.099 mmol) and BINAP (62 mg, 0.099 mmol) were dissolved in THF (10 mL) and heated at 100° C. for 64 hr, cooled to RT, partitioned between EtOAc and brine. The organic layer was dried (MgSO4), filtered, concentrated, and purified by SiO2 chromatography (40 g SiO2, hexanes/EtOAc 0-35% EtOAc) to give 158 mg of benzhydrylidene-[6-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-amine as a yellow liquid (36% yield).

Provenance & Evidence