Pyridine → HCID 21480487, compound

Participants

Reaction Steps

To a stirred solution of the product from Step F (2.50 g, 7.3 mmol) in pyridine (10.0 mL) was added p-toluenesulfonyl chloride (4.50 g, 23.0 mmol) at room temperature. After 16 h, brine (50 mL) was added and the mixture extracted with ethyl acetate (4×50 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4), and evaporated. The residue was dissolved in THF (10 mL) and 2-methoxyethylamine (6.40 mL, 73.0 mmol) was added followed by solid barium carbonate (4.30 g, 22.0 mmol); this mixture was refluxed for 36 h. The excess of amine and THF were removed by evaporation, a saturated aqueous solution of ammonium chloride (50 mL) was added and the mixture was extracted with ethyl acetate (4×50 mL). The combined extracts were washed with brine (20 mL), dried (MgSO4), and evaporated to a residue which was purified by column chromatography (silica, gradient, 30% to 60% ethyl acetate-hexane) to give a solid (1.25 g, 45%). Recrystallization from methanol gave white crystals (0.75 g): mp. 224°-225° C.

Provenance & Evidence