Cesium carbonate → 2-[1-(1-benzhydryl-azetidin-3-yl)-6-fluoro-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde

Participants

Reaction Conditions

Reaction Steps

In a microwave vial 2-(6-fluoro-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (300 mg, 0.73 mmol) was dissolved in DMF (6 ml) and cesium carbonate (713 mg, 2.19 mmol) and methanesulfonic acid 1-benzhydryl-azetidin-3-yl ester (347 mg, 1.09 mmol) were added. The vial was sealed and heated in a microwave reactor at 100° C. 3 h. The reaction was cooled, quenched with water and extracted with EtOAc (2×). The combined organics were washed with water and brine then dried over MgSO4 and concentrated. The crude residue was purified by silica gel chromatography with 20% to 30% EtOAc/hexanes to provide 176 mg (38%) of 2-[1-(1-benzhydryl-azetidin-3-yl)-6-fluoro-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as an orange foam.

Provenance & Evidence