Nitrogen → HCID 131729997, compound

HRID 2064992Notes

Reaction equation

HRID 2064992 reaction equation
N#N.Br[C:4]1[CH:9]=[C:8]([C:10]([CH3:18])([CH3:17])[O:11][SiH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:7]=[CH:6][N:5]=1.[Li]CCCC.CN(C)[C:26](=[O:28])[CH3:27].[NH4+].[Cl-]>CCOCC>[C:13]([SiH2:12][O:11][C:10]([CH3:18])([CH3:17])[C:8]1[CH:7]=[CH:6][N:5]=[C:4]([C:26](=[O:28])[CH3:27])[CH:9]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

7

Reactant 5

HCID 947NitrogenHCID 25517Ammonium ChlorideHCID 31374DimethylacetamideHCID 131729998HCID 131729998, compoundHCID 178418339Butyllithium

Product 1

HCID 131729997HCID 131729997, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), to a solution of 2-bromo-4-(tert-butyl-dimethyl-silanyloxymethyl)-pyridine (1.04 g, 3.44 mmol) in dry Et2O (50 mL) was added n-BuLi (1.60 mL of a 2.5M solution in hexanes, 3.96 mmol) at −78° C. The reaction mixture was then stirred for 1 h at −78° C. before N,N-dimethylacetamide (0.64 mL, 6.88 mmol) was added dropwise. The reaction mixture was allowed to warm up to rt and stirred at this temperature for 10 min. Sat. aq. NH4Cl (20 mL) was added, the layers separated and the aq. layer extracted with Et2O (3×30 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvent was removed under reduced pressure. Purification of the residue by FC (20:1 to 5:1 hept-EA) gave the title compound as a pale yellow oil. TLC: rf (1:2 hept-EA)=0.64. LC-MS-conditions 02: tR=1.12 min; [M+H]+=265.84.

Workup

  1. additionwas added dropwise
  2. customthe layers separated
  3. extractionthe aq. layer extracted with Et2O (3×30 mL)
  4. dry with materialextracts were dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customPurification of the residue by FC (20:1 to 5:1 hept-EA)

Sources & evidence

ORD record
ord-345f5ca298ab427686ee94664eee4ab5
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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