反应详情

温度

90 °C

In a pressure tube 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide (162 mg, 0.30 mmol) and 1-ethyl-1H-pyrazole-4-boronic acid pinacol ester (80 mg, 0.36 mmol) were dissolved in DME (3.0 mL). Aqueous K2CO3 (2.0 M, 0.45 mL, 0.90 mmol) and Pd(PPh3)4 (17 mg, 0.015 mmol) were added and the mixture degassed with a gentle stream of N2 for 15 min. The vial was then sealed and heated at 90° C. for 6 h. The reaction mixture was 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 (20-100% EtOAc/hexane) to afford 125 mg (75%) of 2-(1-ethyl-1H-pyrazol-4-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [(R)-2,2-dimethyl-1-(pyrrolidine-1-carbonyl)-propyl]-amide as a light brown foam.

1. customthe mixture degassed with a gentle stream of N2 for 15 min
2. customThe vial was then sealed
3. temperatureThe reaction mixture was cooled to room temperature
4. customquenched with H2O
5. extractionextracted with EtOAc
6. washThe organic extracts were washed with brine
7. dry with materialdried over MgSO4
8. concentrationconcentrated
9. customThe residue was purified by SiO2 chromatography (20-100% EtOAc/hexane)