Iodoethane → 2-Ethyl-2-(4-iodo-2-pyridyl)butanenitrile

HRID 331516Notes

Reaction equation

HRID 331516 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH:8]([CH2:11][CH3:12])[C:9]#[N:10])[CH:3]=1.I[CH2:14][CH3:15].NC1N=CC(C2C=CN=C(C3(C#N)CCOCC3)C=2)=NC=1C1ON=C(C2C=CC(CNC)=CC=2)C=1>C1(C)C=CC=CC=1.O>[CH2:11]([C:8]([C:4]1[CH:3]=[C:2]([I:1])[CH:7]=[CH:6][N:5]=1)([CH2:14][CH3:15])[C:9]#[N:10])[CH3:12]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 708186554-[4-[5-Amino-6-[3-[4-(methylaminomethyl)phenyl]isoxazol-5-yl]pyrazin-2-yl]-2-pyridyl]tetrahydropyran-4-carbonitrileHCID 708186982-(4-Iodo-2-pyridyl)butanenitrile

Product 1

HCID 708187472-Ethyl-2-(4-iodo-2-pyridyl)butanenitrileYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

Crude 2-(4-iodo-2-pyridyl)butanenitrile (270 mg, 0.9923 mmol) was added to a solution of iodoethane (309.6 mg, 158.8 μL, 1.985 mmol) and bis(trimethylsilyl)azanide (sodium ion (1)) (992.3 μL of 1 M, 0.9923 mmol) in toluene (2 mL) at 0° C. The solution was stirred at 0° C. for 10 minutes. Reaction mixture was diluted with water and the product extracted with dichloromethane (×3). Organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo. (297.8 mg, assumed 100% yield). LC/MS m/z 301.02 [M+H]+

Workup

  1. customReaction mixture
  2. extractionthe product extracted with dichloromethane (×3)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-447bf177edba45f2ab934bf213c5ca3b
Source dataset
uspto-grants-2014_11
Patent number
US08877759B2

Reaction notes

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