Nitrogen → 3-Acetyl-5-bromopyridine

HRID 2064971Notes

Reaction equation

HRID 2064971 reaction equation
N#N.Br[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([Br:10])[CH:9]=1.[Li]CCCC.[NH4+].[Cl-].[CH3:18][CH2:19][O:20]CC>CCCCCC>[Br:10][C:8]1[CH:9]=[C:4]([C:19](=[O:20])[CH3:18])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 947NitrogenHCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 693693,5-DibromopyridineHCID 178418339Butyllithium

Product 1

HCID 8204233-Acetyl-5-bromopyridine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a suspension of 3,5-dibromopyridine (2.39 g, 10.00 mmol) in ether (70.0 mL) was treated at −78° C. with n-BuLi (4.0 mL of a 2.5M solution in hexane, 10.00 mmol). The reaction mixture was stirred for 30 min before N,N-dimethylacetaminde (1.50 mL, 16.13 mmol) was added and the solution was then allowed to warm to rt over 1 h. Sat. aq. NH4Cl was then added and the aq. layer was extracted with Et2O (2×50 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (10:1 hept-EA) gave the title compound as a white solid. TLC: rf (19:1 CH2Cl2-MeOH)=0.57. LC-MS-conditions 02: tR=0.80 min.

Workup

  1. additionwas added
  2. extractionthe aq. layer was extracted with Et2O (2×50 mL)
  3. dry with materialextracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (10:1 hept-EA)

Sources & evidence

ORD record
ord-9fb01af407b840279399f8f729de74d4
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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