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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence