Dimethylformamide → 5-Bromo-4-methylpyridine-3-carbaldehyde

HRID 1454932Notes

Reaction equation

HRID 1454932 reaction equation
C([Li])CCC.Br[C:7]1[CH:8]=[N:9][CH:10]=[C:11]([Br:14])[C:12]=1[CH3:13].CN([CH:18]=[O:19])C.[NH4+].[Cl-]>CCCCCC>[Br:14][C:11]1[C:12]([CH3:13])=[C:7]([CH:18]=[O:19])[CH:8]=[N:9][CH:10]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 8193383,5-Dibromo-4-methylpyridine2×HCID 178418339Butyllithium

Product 1

HCID 222383375-Bromo-4-methylpyridine-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-100 °C

Procedure

Under argon, an n-butyllithium solution in hexane (1.55N, 4.6 ml) is added dropwise to a 3,5-dibromo-4-methylpyridine solution (intermediate 10.1, 1.76 g, 7 mmol) kept at −100° C. After stirring for 5 min, DMF (0.84 ml, 1.54 equiv.) is added dropwise. The stirring is maintained for 20 min at −100° C. and then for 1 h at −78° C. An aqueous NH4Cl solution is added and the reaction mixture is extracted with a diethyl ether/water mixture. The yellow solid obtained is purified on silica gel (100 g), eluting with AcOEt/petroleum ether (1/4).

Workup

  1. customkept at −100° C
  2. waitfor 1 h at −78° C
  3. extractionthe reaction mixture is extracted with a diethyl ether/water mixture
  4. customThe yellow solid obtained
  5. customis purified on silica gel (100 g)
  6. washeluting with AcOEt/petroleum ether (1/4)

Sources & evidence

ORD record
ord-0077a2d412244a438f2a6e1f82095496
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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