Sodium hydride → HCID 58335249, compound

HRID 2060628Notes

Reaction equation

HRID 2060628 reaction equation
[H-].[Na+].[OH:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[Br:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16]Br)[N:11]=1>CN(C)C=O>[Br:9][C:10]1[N:11]=[C:12]([CH2:16][O:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66774Methyl GlycolateHCID 129547962-Bromo-6-(bromomethyl)pyridine

Product 1

HCID 58335249HCID 58335249, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (0.50 g, 12.4 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added methyl hydroxyacetate (1.0 g, 11.3 mmol) and 2-bromo-6-(bromomethyl)pyridine (Example 8, Step 1) (3.4 g, 13.5 mmol). After stirring for 5 hours, the reaction was quenched with an isopropanol/methanol solution. The reaction mixture was poured into ice water and extracted with ether. The organic phase was dried over MgSO4, filtered and concentrated in vacuo. The resulting material was purified by flash chromatography (silica, 10% ethyl acetate/hexanes) to afford the title compound. 1H NMR (400 MHz CDCl3): δ 7.55 (t, 1H), 7.48 (d, 1H), 7.39 (d, 1H), 4.71 (s, 2H), 4.22 (s, 2H), 3.77 (s, 3H).

Workup

  1. customthe reaction was quenched with an isopropanol/methanol solution
  2. additionThe reaction mixture was poured into ice water
  3. extractionextracted with ether
  4. dry with materialThe organic phase was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting material was purified by flash chromatography (silica, 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-1bfc80e347e94bafab36e6df82a6a48c
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

Loading…