Lithium Bromide → N-(3-Bromopropyl)-2-pyridinecarboxamide

Participants

Reaction Steps

A mixture of methanesulfonic acid 3-[(pyridine-2-carbonyl)-amino]-propyl ester (Example 57a) (1.96 g) and lithium bromide (3.29 g) in acetone (19 mL) was heated to reflux for 2 h. The reaction mixture was cooled to room temperature, concentrated in vacuo and the residue partitioned between EtOAc/H2O (60 mL, 1:1). The phases were separated and the aqueous phase further extracted with EtOAc (2×25 mL). The combined organics were dried (MgSO4) and concentrated in vacuo to a brown oil which solidified on standing. Purification by silica gel chromatography eluting with 0-100% EtOAc/cyclohexane gives the sub-titled compound (1.5 g) as a white solid.

Provenance & Evidence