Diisopropylethylamine → 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-4-yl-ethyl)-amide

Participants

Reaction Steps

2-Bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (320 mg, 0.86 mmol), 1-(pyridin-4-yl)ethanamine (105 mg, 0.86 mmol) and DIPEA (449 mg, 2.58 mmol) were combined with DMF (5 mL) to give a yellow solution. HATU (327 mg, 0.86 mmol) was added and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was diluted with brine and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with water and brine then dried with MgSO4, filtered and concentrated in vacuo to afford 380 mg (93%) of 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1-pyridin-4-yl-ethyl)-amide as a red oil. MS: (M+H)+=477.

Provenance & Evidence