反应详情

温度

80 °C

In a round-bottomed flask, 2-bromo-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde (400 mg, 1.12 mmol) and 6-chloro-1-methyl-3-tributylstannyl-1H-indazole (1.11 g, 1.7 mmol) were dissolved in DMF (10 mL). The flask was evacuated and backfilled with argon then tetrakis(triphenylphosphine)palladium(0) (65 mg, 0.056 mmol) and copper(I) iodide (43 mg, 0.23 mmol) were added. The reaction mixture was stirred at 80° C. in an oil bath overnight then cooled to room temperature, quenched with water and extracted with diethyl ether (2×). The combined organic layers were washed twice with water and once with brine then dried over sodium sulfate, filtered and concentrated. The residue was absorbed on silica gel and chromatographed with EtOAc/hexanes (gradient 0-30% EtOAc) to provide 416 mg (84%) of 2-(6-chloro-1-methyl-1H-indazol-3-yl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carbaldehyde as a yellow solid.

1. customThe flask was evacuated
2. temperaturethen cooled to room temperature
3. customquenched with water
4. extractionextracted with diethyl ether (2×)
5. washThe combined organic layers were washed twice with water and once with brine
6. dry with materialthen dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was absorbed on silica gel
10. customchromatographed with EtOAc/hexanes (gradient 0-30% EtOAc)