Ethyl Acetate → HCID 22217916, compound

HRID 351672Notes

Reaction equation

HRID 351672 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.[C:9](CCCO)#[N:10].[CH3:15][Si](C)(C)[N-][Si](C)(C)C.[Na+].CCO[C:28]([CH3:30])=[O:29]>CS(C)=O>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([O:29][CH2:28][CH:30]([C:9]#[N:10])[CH3:15])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 693532,5-DibromopyridineHCID 2207054-hydroxybutanenitrileHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 22217916HCID 22217916, compoundYield 39.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 2,5-dibromopyridine (500 mg, 2.1 mmol) and 3-cyano-1-propanol (270 mg, 3.1 mmol) in DMSO (2 mL) was added IM sodium hexamethyldisilazide (2.1 mL, 2.1 mmol). The reaction was stirred at room temperature overnight. EtOAc was added to the reaction and the mixture was washed with water (2×10 mL). The EtOAc fraction was dried over anhydrous sodium sulfate and evaporated on a rotary evaporator. The crude product was purified by flash column chromatography over silica gel using 40%EtOAc/hexanes to give 200 mg of 5-bromo-2-cyanopropyloxypyridine as a pale yellow solid (39.3%).

Workup

  1. washthe mixture was washed with water (2×10 mL)
  2. dry with materialThe EtOAc fraction was dried over anhydrous sodium sulfate
  3. customevaporated on a rotary evaporator
  4. customThe crude product was purified by flash column chromatography over silica gel using 40%EtOAc/hexanes

Sources & evidence

ORD record
ord-e70688de0e9541db8fb4b5d3afdf585e
Source dataset
uspto-grants-2004_06
Patent number
US06743788B2

Reaction notes

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