2,2'-Bipyridine → HCID 89467172, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 6-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate (510 mg, 2.260 mmol), cyclopropylboronic acid (388 mg, 4.52 mmol), sodium carbonate (479 mg, 4.52 mmol) in 1,2-Dichloroethane (DCE) (150 mL) was added a suspension of copper(II) acetate (411 mg, 2.260 mmol), 2,2′-bipyridine (353 mg, 2.260 mmol) in hot 1,2-dichloroethane. The contents were heated at 70° C. for 16 hours. Added cyclopropylboronic acid (388 mg, 4.52 mmol), sodium carbonate (479 mg, 4.52 mmol) followed by copper(II) acetate (411 mg, 2.260 mmol), 2,2′-bipyridine (353 mg, 2.260 mmol) in hot 1,2-dichloroethane and heated at 70° C. for 16 hours. The contents were cooled to room temperature followed by addition of 100 mL of saturated NH4Cl solution and the phases were separated. The aqueous layer was extracted with DCM twice. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was purified via silica gel chromatography (eluent: 0% to 20% gradient EtOAc:Hex). The product was collected as 310 mg. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.95-1.26 (m, 4 H), 2.53 (s, 3 H), 3.75-3.91 (m, 1 H), 3.96 (s, 3 H), 7.55 (s, 1 H). LCMS(ES) [M+H]+266.0

Provenance & Evidence