Methyl iodide → 5-Bromo-1-methylpyridin-2(1H)-one

HRID 1292737Notes

Reaction equation

HRID 1292737 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](=[O:8])[NH:4][CH:3]=1.[C:9](=O)([O-])[O-].[Cs+].[Cs+].CI>C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5](=[O:8])[N:4]([CH3:9])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 5995285-Bromo-2-hydroxypyridine

Product 1

HCID 130240275-Bromo-1-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

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).

Workup

  1. extractionextracted sequentially with two portions of saturated aqueous sodium bicarbonate and brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customPurification by HPLC (silica gel, 60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1d6d689610124c4482c405f39468c4a1
Source dataset
uspto-grants-2007_07
Patent number
US07238683B2

Reaction notes

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