Acetic Acid → HCID 89852127, compound

Participants

Reaction Steps

To a solution of ethyl 2-(3-formyl-1H-pyrazol-1-yl)nicotinate (400 mg, 1.631 mmol) and morpholine (220 μl, 2.53 mmol) in acetonitrile (25 mL) NaCNBH4 (130 mg, 2.069 mmol) was added, and the pH adjusted to 5-6 by adding glacial acetic acid (110 μL, 1.922 mmol). The mixture was stirred at room temperature for 1 h, another portion of NaCNBH4 (30 mg, 0.477 mmol) added and stirred for 2 hrs. For work up the mixture was concentrated, dissolved in 100 mL of dichloromethane, washed subsequently with water and brine, dried (MgSO4), filtered off and concentrated to give 710 mg of the crude title product. Purification by chromatography over silica gel (CH2Cl2/3%-5% methanol) and concentration yielded 518 mg of the title compound as clear oil; ESI-MS [M+H]+: 317.20.

Provenance & Evidence