Cyclopropylboronic acid → 2-cyclopropyl-7-iodo-2H-pyrazolo[4,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

N-Sodiohexamethyldisilazane (3.40 mL, 2.041 mmol), N,N-dimethylpyridin-4-amine (748 mg, 6.12 mmol), 7-iodo-2H-pyrazolo[4,3-b]pyridine (500 mg, 2.041 mmol), diacetoxycopper (371 mg, 2.041 mmol) and cyclopropylboronic acid (351 mg, 4.08 mmol) were combined in toluene (15 mL) and sparged with air. The mixture was heated at 95° C. overnight. The mixture was then cooled and poured into saturated NH4Cl and extracted with EtOAc (2×). The combined organic layers were dried over Na2SO4 and concentrated to give a residue which was purified on silica column chromatography eluted with EtOAc/Hexanes (0-97%) using a step gradient and then to 98% EtOAc to give 2-cyclopropyl-7-iodo-2H-pyrazolo[4,3-b]pyridine. The other fractions were further purified on a second silica column chromatography eluted with EtOAc/Hexanes (0-50%) using a step gradient and then to 90% EtOAc to give the title compounds. MS [M+H] found 286.1.

Provenance & Evidence