Isobutyronitrile → 2-(5-Bromopyridin-2-yl)-2-methylpropanenitrile

HRID 1046248Notes

Reaction equation

HRID 1046248 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9](#[N:13])[CH:10]([CH3:12])[CH3:11]>C1(C)C=CC=CC=1>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([C:10]([CH3:12])([CH3:11])[C:9]#[N:13])=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 6559IsobutyronitrileHCID 693532,5-Dibromopyridine

Product 1

HCID 115866222-(5-Bromopyridin-2-yl)-2-methylpropanenitrile

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

NaN[(SiCH3)3]2 (1 M in tetrahydrofuran, 6.3 mL) was added dropwise to a solution of 2,5-dibromo-pyridine (1.50 g) and isobutyronitrile (0.58 mL) in toluene (15 mL) chilled in an ice bath and kept under argon atmosphere. The resulting mixture was further stirred with cooling for 1 h and then at room temperature overnight. The mixture was filtered and the filtrate was washed with water, 10% aqueous K2CO3 solution, and brine. The organic phase was dried (MgSO4) and the solvent was evaporated. The residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->95:5) to furnish the title compound. Yield: 0.26 g (18% of theory); Mass spectrum (ESI+): m/z=220/222 (Br) [M+H]+.

Workup

  1. temperaturechilled in an ice bath
  2. temperaturewith cooling for 1 h
  3. customat room temperature
  4. customovernight
  5. filtrationThe mixture was filtered
  6. washthe filtrate was washed with water, 10% aqueous K2CO3 solution, and brine
  7. dry with materialThe organic phase was dried (MgSO4)
  8. customthe solvent was evaporated
  9. customThe residue was purified by chromatography on silica gel (dichloromethane/methanol 99:1->95:5)

Sources & evidence

ORD record
ord-8b274179b7dc43418056c854bf3100a7
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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