Imidazo[1,2-a]pyridine-7-carbonitrile, 3-iodo- → 2-(7-cyano-imidazo[1,2-a]pyridin-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide

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2-Bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide (100 mg, 0.196 mmol) and hexamethyltin (72 mg, 0.22 mmol) were combined in a nitrogen sparged toluene (5 ml) solution. Tetrakis(triphenylphosphine)palladium(0) (19.5 mg, 0.17 mmol) was added and the solution heated to 95° C. for 2 h. The reaction was cooled and 3-iodo-imidazo[1,2-a]pyridine-7-carbonitrile (54 mg, 0.2 mmol) was added with additional tetrakis(triphenylphosphine)palladium(0) (20 mg, 0.02 mmol). The mixture was heated at 100° C. for 14 h, cooled and directly purified by silica gel chromatography to afford 2-(7-cyano-imidazo[1,2-a]pyridin-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid ((S)-2-methoxy-1-methyl-ethyl)-amide.

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