Water → HCID 68616364, compound

HRID 1528602Notes

Reaction equation

HRID 1528602 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][C:11]#[N:12])=[N:8][CH:9]=1.Br[CH2:14][CH2:15][O:16][CH2:17][CH2:18]Br.O>CN(C)C=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:11]#[N:12])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 21521Bis(2-bromoethyl) etherHCID 24758Sodium hydrideHCID 29927881(5-Bromopyridin-2-yl)acetonitrile

Product 1

HCID 68616364HCID 68616364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

NaH (55% in mineral oil, 0.23 g) was added to a solution of (5-bromo-pyridin-2-yl)-acetonitrile (0.50 g) in N,N-dimethylformamide (5 mL) chilled in an ice bath. The resulting mixture was stirred for 10 min in the cooling bath prior to the dropwise addition of bis(2-bromoethyl)ether (0.35 mL) dissolved in N,N-dimethylformamide (2 mL). The mixture was stirred with cooling for 2 h and at room temperature for 1 h. Water was added and the resulting mixture was extracted with ethyl acetate. The combined extracts were washed with brine and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1) to give the title compound as a colorless oil. Yield: 0.62 g (91% of theory); LC (method 1): tR=1.70 min; Mass spectrum (ESI+): m/z=267/269 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. stirringThe mixture was stirred
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with brine
  5. dry with materialdried (MgSO4)
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed on silica gel (cyclohexane/ethyl acetate 4:1→1:1)

Sources & evidence

ORD record
ord-411fdb1194fe4e50b0839d62772cd91b
Source dataset
uspto-grants-2015_07
Patent number
US09090605B2

Reaction notes

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