Diisopropylethylamine → 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide

Participants

Reaction Steps

2-Bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (300 mg, 0.81 mmol), 1-(pyridin-3-yl)ethanamine (148 mg, 1.21 mmol) and DIPEA (0.42 mL, 2.42 mmol) were combined with DMF (5 mL) to give a yellow solution. Then HATU (306 mg, 0.81 mmol) was added and the reaction mixture stirred at room temperature for 4 h. The reaction mixture was diluted with brine and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with water and brine then dried over MgSO4, filtered and concentrated in vacuo to afford 350 mg (91%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-3-yl-ethyl)-amide as a yellow oil. MS: (M+H)+=477.

Provenance & Evidence