反应详情

温度

80 °C

Methyl zinc chloride (3.35 mL, 6.70 mmol) was added to 3-bromo-4-chloro-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.23 mmol) and Pd(PPh3)4 (0.129 g, 0.111 mmol) in THF (10 mL). The reaction was then heated to 80° C. for 2 hours, cooled to room temperature, and quenched with saturated NH4Cl. The resulting solids were filtered and discarded. The filtrate was diluted with DCM (500 mL) and was washed with water. The combined organic fractions were dried, filtered, and concentrated to give a crude solid that was purified by column chromatography (2:1 DCM:hexanes) to give 4-chloro-3-methyl-5-phenyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.75 g, 87.7% yield).

1. temperaturecooled to room temperature
2. customquenched with saturated NH4Cl
3. filtrationThe resulting solids were filtered
4. additionThe filtrate was diluted with DCM (500 mL)
5. washwas washed with water
6. customThe combined organic fractions were dried
7. filtrationfiltered
8. concentrationconcentrated
9. customto give a crude solid that
10. customwas purified by column chromatography (2:1 DCM:hexanes)