Sodium hydride → HCID 58335249, compound

HRID 385843Notes

Reaction equation

HRID 385843 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>[CH3:8][O:7][C:5](=[O:6])[CH2:4][O:3][CH2:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([Br:9])[N:11]=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, 12.38 mmol) in N,N-dimethylformamide (20 mL) at 0° C. was added a mixture of methyl hydroxyacetate (1.0 g, 11.25 mmol) and 2-bromo-6-(bromomethyl)pyridine (Example 190, Step 1) (3.4 g, 13.5 mmol) dropwise. After stirring for 5 hours, the reaction was quenched with iso-propanol/methanol solution. The reaction mixture was poured onto iced water and extracted with ether. The organic phase was dried over MgSO4, filtered and evaporated. The crude mixture was purified by silica gel column and eluted with ethyl acetate:petroleum ether (1:10) 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. additionwas added
  2. customthe reaction was quenched with iso-propanol/methanol solution
  3. additionThe reaction mixture was poured onto iced water
  4. extractionextracted with ether
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude mixture was purified by silica gel column
  9. washeluted with ethyl acetate:petroleum ether (1:10)

Sources & evidence

ORD record
ord-f23ccc46adac48a99c04aec3cf19a027
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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