Butyl iodide → 3-Bromo-6-butoxypicolinonitrile

HRID 1479487Notes

Reaction equation

HRID 1479487 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](=[O:8])[NH:4][C:3]=1[C:9]#[N:10].C(=O)([O-])[O-].[K+].[K+].I[CH2:18][CH2:19][CH2:20][CH3:21]>CC(C)=O>[Br:1][C:2]1[C:3]([C:9]#[N:10])=[N:4][C:5]([O:8][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 668751023-Bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile

Product 1

HCID 668756953-Bromo-6-butoxypicolinonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3-bromo-6-oxo-1,6-dihydropyridine-2-carbonitrile (from Example 15/Step 2) (1.0 eq.), potassium carbonate (1.3 eq.), and 1-iodobutane (1.2 eq.) in acetone (0.3 M) was stirred at 70° C. overnight. The solvent was concentrated en vacuo, and the resulting residue was taken up in water and ethyl acetate. The aqueous layer was extracted with ethyl acetate three times. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vacuo. The crude product was purified by a COMBIFLASH® system (ISCO) using 0-30% ethyl acetate in hexane to give a colorless solid.

Workup

  1. customwas stirred at 70° C. overnight
  2. concentrationThe solvent was concentrated en vacuo
  3. extractionThe aqueous layer was extracted with ethyl acetate three times
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vacuo
  7. customThe crude product was purified by a COMBIFLASH® system (ISCO)
  8. customto give a colorless solid

Sources & evidence

ORD record
ord-12dbb2c9df1f48cbbf75a52fff9faa38
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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