Potassium Phosphate, Tribasic → 6-Cyclopropylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a sealable vial under nitrogen was added 2-amino-6-bromo-pyridine (1.6 g), cyclopropyl boronic acid (1.03 g) (prepared according to Wallace et al. Tetrahedron Lett. 2002, 43, 6987-6990), potassium phosphate (6.87 g), tricyclohexylphosphine (0.260 g) followed by water (2 mL) and toluene (40 mL). Pd(OAc)2 (0.104 g) was then added and the vial was sealed and heated at 100° C. over 16 hours. The reaction was then allowed to cool to ambient temperature and diluted with water and ethyl acetate. The phases were separated and the aqueous phase was extracted with more ethyl acetate (3×). The combined phases were washed with brine and dried over sodium sulfate. Filtration and evaporation of the volatiles afforded a crude residue which was purified via ISCO Combiflash chromatography using ethyl acetate/heptane as the eluent to give the desired 6-cyclopropyl-pyridin-2-ylamine as yellow solid (0.450 g).

Provenance & Evidence