Sodium hydride → Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylate

HRID 392020Notes

Reaction equation

HRID 392020 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][OH:7])=[N+:2]=[N-:3].[H-].[Na+].[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19](Br)[CH:18]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:16]=1)=[O:14])[CH3:11]>CN(C=O)C>[CH2:10]([O:12][C:13]([C:15]1[CH:20]=[C:19]([O:7][CH2:6][CH2:5][CH2:4][N:1]=[N+:2]=[N-:3])[CH:18]=[C:17]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[N:16]=1)=[O:14])[CH3:11]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109969743-Azidopropan-1-olHCID 13794409Diethyl 4-bromopyridine-2,6-dicarboxylate

Product 1

HCID 22323654Diethyl-4-(3-azidopropoxy)-2,6-pyridinedicarboxylateYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

3-Azido-1-propanol (0.266 mL, 3.64 mmol) was dissolved in DMF (5 mL) and cooled to 0° C. NaH (146 mg, 3.64 mmol) was added and the mixture was stirred for 15 minutes. Diethyl-4-bromo-2,6-pyridinedicarboxylate dissolved in DMF (5 mL) was added to the reaction mixture dropwise. The reaction was complete as indicated by TLC in 1 hour. The reaction mixture was partitioned between CH2Cl2 and water. The water was separated and extracted with CH2Cl2. The CH2Cl2 layers were combined, dried (MgSO4) and concentrated to an oil. The oil was purified by silica gel flash column chromatography to give a yield of 40% of the title compound.

Workup

  1. additionwas added to the reaction mixture dropwise
  2. waitas indicated by TLC in 1 hour
  3. customThe reaction mixture was partitioned between CH2Cl2 and water
  4. customThe water was separated
  5. extractionextracted with CH2Cl2
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to an oil
  8. customThe oil was purified by silica gel flash column chromatography

Sources & evidence

ORD record
ord-4aaa52ed25f447a8b5acc259498403ac
Source dataset
uspto-grants-2004_10
Patent number
US06800444B1

Reaction notes

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