Sodium hydride → HCID 86596528, compound

HRID 730064Notes

Reaction equation

HRID 730064 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])#[N:4].Br[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][N:15]=1.[Cl-].[NH4+]>CS(C)=O>[Br:20][C:17]1[CH:18]=[CH:19][C:14](=[C:5]([C:3]#[N:4])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[NH:15][CH:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 693532,5-DibromopyridineHCID 70693tert-Butyl cyanoacetate

Product 1

HCID 86596528HCID 86596528, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a suspension of NaH (66.4 g, 60% oil dispersion) in dry DMSO (1.5 L) was added t-butyl cyanoacetate (243 mL) at 18-25° C. for 1 hour, the mixture was stirred at room temperature for 2 hours. 2,5-Dibromopyridine (150 g) was added to the resulting mixture, the mixture was stirred at 120° C. for 6.5 hours. After cooling, the mixture was poured into saturated ammonium chloride solution, the resulting precipitates were collected by filtration, washed with water and cooled EtOH to give t-butyl (5-bromo-2(1H)-pyridinylidene)cyanoacetate (166 g).

Workup

  1. stirringthe mixture was stirred at 120° C. for 6.5 hours
  2. temperatureAfter cooling
  3. customthe resulting precipitates
  4. filtrationwere collected by filtration
  5. washwashed with water
  6. temperaturecooled EtOH

Sources & evidence

ORD record
ord-a18e1ed009b54ef2997dcd02f820bbae
Source dataset
uspto-grants-2009_09
Patent number
US07582659B2

Reaction notes

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