2-Pyridinecarboxaldehyde → HCID 22319133, compound

HRID 547734Notes

Reaction equation

HRID 547734 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](Br)=[CH:5][N:4]=1.C([Li])CCC.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]=[O:22].[Cl-].[NH4+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][N:15]=2)[OH:22])=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 142732-PyridinecarboxaldehydeHCID 25517Ammonium ChlorideHCID 27348955-Bromo-2-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 22319133HCID 22319133, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

50 ml of a tetrahydrofuran solution containing 3.00 g of 2-methoxy-5-bromopyridine was cooled to −78° C., followed by the dropwise addition of 10 ml of n-butyl lithium (1.6M hexane solution). After the completion of the dropwise addition, 1.70 g of picoline aldehyde was immediately added thereto, followed by stirring at −78° C. for 1 hour, to return the mixture slowly to room temperature. To the mixture was added a saturated aqueous solution of ammonium chloride, and then it was extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, and then dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel chromatography (ethyl acetate), to give 1.53 g of the title compound as a pale yellow solid.

Workup

  1. additionwas immediately added
  2. customslowly to room temperature
  3. extractionit was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe resulting residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b2927f6231b94c2e9e7cedfddc694b08
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

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