6-Methoxy-2-pyridinecarbonitrile → 1-(6-Methoxypyridin-2-YL)cyclopropan-1-amine

Participants

Reaction Steps

To a solution of 6-methoxy-pyridine-2-carbonitrile (1.50 g, 11.2 mmol) in THF (75 mL) at room temperature was added Ti(OiPr)4 (7.21 mL, 24.6 mmol). EtMgBr (14.9 mL, 44.7 mmol) was added dropwise. and the clear brown solution became heterogeneous. The reaction mixture was stirred for 1 h at room temperature. The reaction was diluted with water (10 mL), extracted with EtOAc (3×25 mL) and dried with MgSO4. After filtration, the solvent was removed in vacuo. The residue was purified by reverse phase HPLC to afford 380 mg (22%) of 1-(6-methoxy-pyridin-2-yl)-cyclopropylamine, m/z 166.3 [M+1]+.

Provenance & Evidence