Hydrochloric Acid → 1H-Indol-2-ylboronic acid

Temperature

-40 °C

To the SEM-protected indole prepared in step 1 (0.99 g, 4.0 mmol) in THF (10 mL) at −40° C. was added n-BuLi (2.5 M in hexanes, 1.9 mL, 4.8 mmol). The mixture was stirred at −40° C. for 1 h and then triisopropyl borate (1.2 mL, 5.2 mmol) was added. The mixture was allowed to warm to room temperature while stirring for 18 h. To the reaction mixture was added 1N HCl (aq). The mixture was stirred at room temperature for 30 minutes. The mixture was then adjusted to pH˜5 using saturated NaHCO3 (aq) The mixture was extracted with ether. The combined ether extracts were washed with water and brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-50% EtOAc/hex over 30 minutes) to provide the indole boronic acid (0.20 g, 17%).

1. temperatureto warm to room temperature
2. stirringwhile stirring for 18 h
3. stirringThe mixture was stirred at room temperature for 30 minutes
4. extractionwas extracted with ether
5. washThe combined ether extracts were washed with water and brine
6. dry with materialdried (Na2SO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe residue was purified by silica gel chromatography (0-50% EtOAc/hex over 30 minutes)

ORD record

ord-a287b6ed2e6c44d996e6c6da898ea065

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729071B2