Isobutyryl chloride → N-[4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridin-2-ylmethyl]-isobutyramide

Participants

Reaction Steps

4-Chloro-3-(tetrahydro-pyran-2-yloxymethyl)-pyridine-2-carbonitrile (30 mg. 0.12 mmol) was dissolved in a mixture of MeOH (0.75 mL) and THF (1 mL). CoCl2 hexahydrate (56 mg. 0.24 mmol) and NaBH4 (45 mg. 1.19 mmol dissolved in 1 mL MeOH) were added. After stirring for 8 min at RT sat. NaHCO3 solution (1 mL) and isobutyryl chloride (125 μL. 1.19 mmol) were added. The solvents were removed in vacuo and the residue was partioned between sat. NH4Cl solution (10 mL) and DCM (10 mL) and extracted with DCM (3×10 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 2:1→1:2) to give the title compound. MS (m/z): 326.8 [M+H+]

Provenance & Evidence