Nitrogen → 6-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinecarboxaldehyde

HRID 42783Notes

Reaction equation

HRID 42783 reaction equation
N#N.Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[N:5]=1.[Li]CCCC.CN([CH:24]=[O:25])C.C([O-])(O)=O.[Na+]>CCOCC.CCCCCC>[CH3:15][C:10]1([C:6]2[N:5]=[C:4]([CH:24]=[O:25])[CH:9]=[CH:8][CH:7]=2)[O:14][CH2:13][CH2:12][O:11]1

Participants

8

Reactant 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 516892Sodium BicarbonateHCID 121642822-Bromo-6-(2-methyl-1,3-dioxolan-2-yl)pyridineHCID 178418339Butyllithium

Product 1

HCID 860859206-(2-Methyl-1,3-dioxolan-2-yl)-2-pyridinecarboxaldehyde

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8058HexaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-6-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (2.21 g, 9.05 mmol) in Et2O (60.0 mL) at −78° C. was added dropwise n-BuLi (3.70 mL of a 2.5M solution in hexane, 9.25 mmol). The reaction mixture was then stirred at −78° C. for 30 min before DMF (0.85 mL, 11.00 mmol) was added dropwise. The reaction mixture was allowed to warm to rt over 1 h. 5% aq. NaHCO3 was added and the mixture was extracted three times with Et2O. The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA to pure EA) gave the title compound as a pale yellow solid.

Workup

  1. additionwas added dropwise
  2. extractionthe mixture was extracted three times with Et2O
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hept-EA to pure EA)

Sources & evidence

ORD record
ord-b6f1e6b0ab7c4d21ab68bddd2add98ac
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Reaction notes

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