Water → 6-Bromo-5-methylpyridine-3-carbaldehyde

HRID 2403610Notes

Reaction equation

HRID 2403610 reaction equation
C([Mg]Cl)(C)C.[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10](Br)=[CH:9][N:8]=1.N1(C=O)CC[O:18][CH2:17]C1.O>C1COCC1>[Br:6][C:7]1[C:12]([CH3:13])=[CH:11][C:10]([CH:17]=[O:18])=[CH:9][N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 20417N-FormylmorpholineHCID 8176802,5-Dibromo-3-methylpyridineHCID 178418918HCID 178418918, compound

Product 1

HCID 447548846-Bromo-5-methylpyridine-3-carbaldehydeYield 71.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under an argon atmosphere, a solution of 2 M isopropylmagnesium chloride in THF (5.5 ml) was cooled to −78° C., and a solution of 2,5-dibromo-3-methylpyridine (2.5 g) in THF (10 ml) was added dropwise. After stirring at the same temperature for 30 minutes, a solution of morpholine-4-carboaldehyde (1.26 g) in THF (5 ml) was added dropwise thereto, followed by elevating the temperature to 0° C. over 30 minutes, followed by stirring at 0° C. for 2 hours. To the reaction mixture was added water, followed by extraction with EtOAc. The organic layer was dried over Na2SO4 and the solvent was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/EtOAc) to obtain 6-bromo-5-methyl nicotine aldehyde (1.42 g).

Workup

  1. customto 0° C.
  2. customover 30 minutes
  3. stirringby stirring at 0° C. for 2 hours
  4. extractionfollowed by extraction with EtOAc
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationthe solvent was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane/EtOAc)

Sources & evidence

ORD record
ord-978362908f82470696915ce19fc85495
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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