Methanol → 1-(Triisopropylsilyl)pyrrole-3-boronic acid

Temperature

-78 °C

To −78° C. solution of 3-bromo-1-(triisopropylsilyl)-1H-pyrrole (0.619 g, 2.288 mmol) in 10 mL THF was added tert-butyllithium (2.83 mL of 1.7 M in Heptane, 4.80 mmol) dropwise. The reaction mixture was stirring at −78° C. for 45 minutes, then trimethylborate (2.38 g, 22.88 mmol) was added. The reaction was stirred for another 45 minutes at −78° C. To this was then added 0.9 mL methanol and water solution (V/V=1:1) and the reaction was allowed warm to room temperature. The reaction mixture was quenched with H2O (30 mL), then extracted with EtOAc (3×30 mL) and the combined organic extracts washed with brine. The organic phase was dried over Na2SO4 and concentrated in vacuo, and used in the next step without further purification.

1. stirringThe reaction was stirred for another 45 minutes at −78° C
2. temperaturethe reaction was allowed warm to room temperature
3. customThe reaction mixture was quenched with H2O (30 mL)
4. extractionextracted with EtOAc (3×30 mL)
5. washthe combined organic extracts washed with brine
6. dry with materialThe organic phase was dried over Na2SO4
7. concentrationconcentrated in vacuo
8. customused in the next step without further purification

ORD record

ord-f3c9ff7386824966b7599ee99336e74b

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07393959B2