1,4-Dioxane → HCID 59456910, compound

Participants

Reaction Steps

A solution of 5-bromo-3-[(2-dimethylamino-ethyl)methyl]pyridin-2-ylamine (490 mg, 1.79 mmol) and 1,1′-carbonyldiimidazole (349 mg, 2.15 mmol) in 1,4-dioxane (15 mL) was heated to 80° C. for 14 h. TLC analysis indicated remaining starting material. After cooling, additional 1,1′-carbonyldiimidazole (349 mg, 2.15 mmol) and 1,4-dioxane (10 mL) were added, and the solution was heated to reflux overnight. The solvent was removed in vacuo. The residue was dissolved in CH2Cl2 (80 mL). The solution was washed with satd NaHCO3, water and brine, dried over Na2SO4 and concentrated. Purification by column chromatography (silica gel, CH2Cl2/MeOH/Et3N, 92:7:1) gave the title compound (270 mg, 50%) as a tan solid: 1H NMR (300 MHz, DMSO-d6) 69.83 (s, 1H), 8.16 (d, J=2.1 Hz, 1H), 7.76 (s, 1H), 4.48 (s, 2H), 3.37 (t, J=6.5 Hz, 2H), 2.40 (t, J=6.5 Hz, 2H), 2.16 (s, 6H).

Provenance & Evidence