Nitrogen → HCID 86650888, compound

HRID 2064973Notes

Reaction equation

HRID 2064973 reaction equation
N#N.Br[C:4]1[CH:5]=[N:6][CH:7]=[C:8]([C:10]2([CH3:15])[O:14][CH2:13][CH2:12][O:11]2)[CH:9]=1.[Li]CCCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>CCOCC.CCCCCC>[CH3:15][C:10]1([C:8]2[CH:9]=[C:4]([CH:24]=[O:25])[CH:5]=[N:6][CH:7]=2)[O:14][CH2:13][CH2:12][O:11]1

Participants

8

Reactant 5

HCID 947NitrogenHCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 7099161HCID 7099161, compoundHCID 178418339Butyllithium

Product 1

HCID 86650888HCID 86650888, compound

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 3-bromo-5-(2-methyl-[1,3]dioxolan-2-yl)-pyridine (450 mg, 1.84 mmol) in Et2O (40.0 mL) at −78° C. was added dropwise n-BuLi (0.72 mL of a 2.5M solution in hexane, 1.88 mmol). The reaction mixture was then stirred at −78° C. for 30 min before DMF (0.17 mL, 2.24 mmol) was added dropwise. The reaction mixture was allowed to warm to rt over 1 h. Sat. aq NH4Cl 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 (10:1 hept-EA to 1:2) gave the title compound as a pale yellow oil. TLC: rf (50:50 hept-EA)=0.21.

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 (10:1 hept-EA to 1:2)

Sources & evidence

ORD record
ord-ce2cc295f050483197597f047eae992a
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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