Isobutyl iodide → HCID 70869094, compound

HRID 1844732Notes

Reaction equation

HRID 1844732 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:11])([CH3:10])[CH3:9])[NH:5][C:4](=[O:12])[CH:3]=1.[H-].[Na+].I[CH2:16][CH:17]([CH3:19])[CH3:18]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([O:12][CH2:16][CH:17]([CH3:19])[CH3:18])[N:5]=[C:6]([C:8]([CH3:9])([CH3:11])[CH3:10])[CH:7]=1

Participants

5

Reactant 3

HCID 10556Isobutyl iodideHCID 24758Sodium hydrideHCID 70869097HCID 70869097, compound

Product 1

HCID 70869094HCID 70869094, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 17b (1.0 g, 4.33 mmol) in dry DMF (10 mL) was added NaH (0.31 g, 13 mmol) under N2 and the mixture was stirred at rt for 1 h. Then 1-iodo-2-methylpropane (1.35 g, 7.3 mmol) was added and the resulting mixture was heated at 80° C. overnight. The mixture was quenched with water (5 mL) and extracted with EA twice. The combined organic layers were washed with brine (3×), concentrated and purified by CC (PE/EA=50/1) to give compound 17c (1.0 g, 91%) as an oil.

Workup

  1. temperaturethe resulting mixture was heated at 80° C. overnight
  2. customThe mixture was quenched with water (5 mL)
  3. extractionextracted with EA twice
  4. washThe combined organic layers were washed with brine (3×)
  5. concentrationconcentrated
  6. custompurified by CC (PE/EA=50/1)

Sources & evidence

ORD record
ord-1da0538b5c714f80b7e771dbf1ff43f0
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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