Dichloromethane → 5-Ethenyl-2-(tetrazol-1-yl)pyridine

Temperature

90 °C

To a stirring solution of 5-bromo-2-(1H-tetrazol-1-yl)pyridine (1.0 g, 4.42 mmol), in EtOH (70 mL) were added bis[(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (0.361 g, 0.442 mmol), potassium vinyl trifluoroborate (1.18 g, 8.85 mmol, 2 equiv.), triethylamine (1.23 mL, 8.85 mmol, 2 equiv), and water (0.5 mL). The reaction mixture was heated to reflux (90° C., oil bath). Upon completion as determined by reverse phase HPLC-MS (1-2 h) and TLC (eluent: 10% ethyl acetate in hexanes), the reaction was cooled to room temperature, and then was diluted with water and extracted with EtOAc. The combined organic layers were washed with brine and dried over MgSO4. The extracts were concentrated and chromatographed over a column of SiO2 (0-20% EtOAc/hexanes as eluent). Evaporation of the solvent yielded the title compound.

1. temperatureThe reaction mixture was heated
2. temperaturethe reaction was cooled to room temperature
3. extractionextracted with EtOAc
4. washThe combined organic layers were washed with brine
5. dry with materialdried over MgSO4
6. concentrationThe extracts were concentrated
7. customchromatographed over a column of SiO2 (0-20% EtOAc/hexanes as eluent)
8. customEvaporation of the solvent

ORD record

ord-9d2ea2b837d646d497c30a2e4526045f

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139585B2