Water → 5-Fluoro-6-isopropenyl-pyridin-2-ylamine

Participants

Reaction Conditions

Reaction Steps

To a solution 6-bromo-5-fluoro-pyridin-2-ylamine (850 mg, 4.45 mmol) in dimethylacetamide (13.5 mL) was added 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (1.09 mL, 5.79 mmol), palladium tetrakis(triphenylphosphine) (514 mg, 445 μmol) and tribasic potassium phosphate (1.89 g, 8.9 mmol) in water (4 mL, 223 mmol). The mixture was sealed in a microwave vial and heated at 150° C. in a microwave for 15 min. Upon cooling, the mixture was diluted with EtOAc, washed with water and brine, concentrated on to silica gel, and chromatographed (20% to 100% EtOAc in hexanes) to give 5-fluoro-6-isopropenyl-pyridin-2-ylamine contaminated with catalyst-derived impurities (−800 mg) that was used directly in the next step without further purification.

Provenance & Evidence