N-methyl-2-pyrrolidone → 6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.1 g, 3.74 mmol), Zn(CN)2 (873 mg, 7.46 mmol), and Pd(PPh3)4 (646 mg, 0.56 mmol) in NMP (25 mL) under nitrogen was heated at 100° C. overnight. After it was cooled to RT, the reaction mixture was partitioned between EtOAc (300 mL) and water (50 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel chromatography using petroleum ether:EtOAc (10:1) as eluting solvents to afford 6-methyl-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (400 mg, 50%). MS (ESI): m/z=242.3 [M+1]+.

Provenance & Evidence