Cesium carbonate → 2-[5-difluoromethoxy-1-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

Participants

Reaction Conditions

Reaction Steps

To a solution of methanesulfonic acid 1-methyl-1H-pyrazol-4-ylmethyl ester (108 mg, 0.57 mmol) in DMF (2 mL) were added 2-(5-difluoromethoxy-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (100 mg, 0.19 mmol) and Cs2CO3 (184 mg, 0.57 mmol). The bright yellow reaction mixture was heated at 90° C. for 2 h then cooled to room temperature, quenched with water and extracted with EtOAc (2×). The combined organics were washed with water (3×) dried over MgSO4 and concentrated. The residue was chromatographed with 50% to 100% EtOAc/hexanes to afford 60 mg (51%) of 2-[5-difluoromethoxy-1-(1-methyl-1H-pyrazol-4-ylmethyl)-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow solid.

Provenance & Evidence