Methyl iodide → 3-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-one

HRID 625944

Reaction equation

HRID 625944 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:16])[NH:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10](=[O:16])[N:11]([CH3:17])[CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 674068463-(benzyloxy)-5-bromopyridin-2(1H)-one

Product 1

HCID 674178603-(benzyloxy)-5-bromo-1-methylpyridin-2(1H)-oneYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(benzyloxy)-5-bromopyridin-2(1H)-one (4.4 g, 15.71 mmol) in DMF (50 mL) was added Cs2CO3 (6.65 g, 20.42 mmol) then iodomethane (1.2 mL, 19.19 mmol) at RT. After stirring overnight the mixture was concentrated. The residue was taken up in H2O and extracted with CH2Cl2 (3×). The combined organic layers were dried (MgSO4), filtered, and concentrated. Flash column (Biotage-SNAP-100 g, 50% EtOAc/hexanes) gave the title compound (3.61 g, 78%) as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.43-7.30 (m, 5 H); 7.05 (d, J=2.4 Hz, 1 H); 6.69 (d, J=2.4 Hz, 1 H); 5.24 (s, 0 H); 5.10 (s, 2 H); 3.55 (s, 3 H). LC/MS (M+H)+ 294/296.

Workup

  1. customat RT
  2. concentrationwas concentrated
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2e504849367b4ef48790d4aa8e71c065
Source dataset
uspto-grants-2016_04
Patent number
US09309199B2

Linked notes

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