Potassium Carbonate → 5-(Prop-1-en-2-yl)pyridin-2-amine

Temperature

80 °C

A mixture of 2 g (11.56 mmol) of 5-bromopyridin-2-amine, 2.39 mL (13.87 mmol) of 4.4.5.5-tetramethyl-2-(prop-1-en-2-yl)-1.3.2-dioxaborolane and 3.83 g (27.74 mmol) of K2CO3 in 30 mL of DME and 10 mL of water is stirred for 5 minutes under argon, followed by addition of 1 g (2.1 mmol) of palladium bis(tri-t-butylphosphine). The reaction medium is heated for 3 hours at 80° C. After cooling to room temperature, the reaction medium is taken up in 40 mL of water and extracted with EtOAc (3×30 mL). The organic phases are washed with 0.5N HCl solution (3×30 mL). The aqueous phases are neutralized with 1N sodium hydroxide solution and then extracted with EtOAc (2×50 mL). The combined organic phases are dried over Na2SO4, filtered and concentrated under reduced pressure. 1.10 g of 5-(prop-1-en-2-yl)pyridin-2-amine are obtained in the form of a yellow solid, which is used without further purification in the following step.

1. temperatureAfter cooling to room temperature
2. extractionextracted with EtOAc (3×30 mL)
3. washThe organic phases are washed with 0.5N HCl solution (3×30 mL)
4. extractionextracted with EtOAc (2×50 mL)
5. dry with materialThe combined organic phases are dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure

ORD record

ord-ffcd29331aa1414daed633032fce4d8b

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08697731B2