Potassium Carbonate → HCID 67386580, compound

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide (125 mg, 0.25 mmol) and 3,4,5-trimethoxyphenylboronic acid (78 mg, 0.37 mmol) were dissolved in DME (2.0 mL). Aqueous K2CO3 (2.0 M, 0.37 mL, 0.74 mmol) and Pd(PPh3)4 (14 mg, 0.012 mmol) were added and the mixture degassed with a gentle stream of N2 for 15 min. The reaction mixture was heated at 90° C. for 1.5 h then cooled to room temperature, quenched with H2O and extracted with EtOAc. The organic extracts were washed with brine, dried over MgSO4, and concentrated. The residue was purified by SiO2 chromatography (50-100% EtOAc/heptane) to afford 146 mg (>100%) of 2-(3,4,5-trimethoxy-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2-(3-cyano-azetidin-1-yl)-1-methyl-2-oxo-ethyl]-amide as a viscous colorless oil.

Provenance & Evidence