2-(5-formyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide → 2-[5-(1-hydroxy-ethyl)-1-methyl-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, 2-(5-formyl-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanylethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide (111 mg, 0.225 mmol) was suspended in THF (3 ml). The pale yellow suspension was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether, 0.23 ml, 0.69 mmol) was added dropwise. The dark red suspension was stirred at 0° C. for 1 h then quenched with saturated aqueous NH4Cl and extracted with dichloromethane (2×). The organic layers were combined, dried over sodium sulfate, filtered and concentrated. The residue was chromatographed over 12 g silica gel with EtOAc/hexanes (gradient: 0-80% EtOAc) to afford 42 mg (37%) of 2-[5-(1-hydroxy-ethyl)-1-methyl-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid isopropylamide as a light yellow solid.

Provenance & Evidence