Dimethylformamide → 4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

2,4-Dichloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine (455 mg. 1.74 mmol) was dissolved in a mixture of DMF (3 mL) and water (30 μL). The following reagents were added subsequently: zinc cyanide (112 mg. 0.95 mmol), zinc dust (9.1 mg. 139 μmol), zinc acetate (25.5 mg. 139 μmol). 1,1′-bis(diphenylphosphino)ferrocene (58 mg. 104 μmol) and tris(dibenzylideneacetone)palladium (0). The reaction mixture was degassed two times and afterwards heated at 95° C. for 4 h. The solvents were removed in vacuo and the residue was pardoned between water (20 mL) and EtOAc (20 mL) and extracted with EtOAc (3×20 ml). The combined organic layers were washed with brine and dried over Na2SO4 filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (elution with hexane/EtOAc 10:1→5:1) to give the title compound. MS (m/z): 253.0 [M+H+].

Provenance & Evidence