Reaction #1379919

Reaction equation

product

3-Bromo-6-oxo-1,6-dihydropyridine

cesium carbonate

methyl iodide

→

title compound

3-Bromo-1-methyl-6-oxo-1,6-dihydropyridine

Solvents

ethyl acetate

Conditions

Workup

1. 1
   Extractionextracted sequentially with two portions of saturated aqueous sodium bicarbonate and brine
2. 2
   Dryingdried over sodium sulfate
3. 3
   Concentrationconcentrated
4. 4
   OtherPurification by HPLC (silica gel, 60% ethyl acetate/hexane)

Procedure

To a solution of 4.38 g of the product from Step A in DMP was added 81 g of cesium carbonate and 30 mL of methyl iodide. The mixture was stirred at ambient temperature overnight, diluted with ethyl acetate, extracted sequentially with two portions of saturated aqueous sodium bicarbonate and brine, dried over sodium sulfate, and concentrated. Purification by HPLC (silica gel, 60% ethyl acetate/hexane) gave the title compound. 1H NMR (500 MHz, CDCl3) δ 7.46 (d, 1H, J=2.7 Hz), 7.38 (dd, 1H, J=2.7, 9.8 Hz), 6.52 (d, 1H, J=9.8 Hz), 3.55 (s, 3H).

Source