Isopropylamine → 2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide

Participants

Reaction Steps

To a solution of 2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (75 mg, 0.16 mmol), HOBt (63 mg, 0.38 mmol) and EDC (72 mg, 0.38 mmol) in DMF was added isopropylamine (84 ul, 0.98 mmol). The reaction mixture was stirred at room temperature for 1.5 h then additional HOBt, EDC, and isopropylamine were added. The reaction mixture was stirred at room temperature overnight then diisopropylethylamine (170 ul, 0.98 mmol) was added. The reaction was stirred for 1 h then quenched with water and extracted with EtOAc (2×). The combined organic layers were washed with 10% citric acid, sat NaHCO3, sat LiCl, and brine then dried over MgSO4 and concentrated. The residue was chromatographed over silica gel with 20% to 100% EtOAc/heptane to afford 30 mg (37%) of 2-(4,6-difluoro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide as a white solid.

Provenance & Evidence