Water → N-(5-Bromo-pyridin-3-ylmethyl)-propionamide

HRID 1774847Notes

Reaction equation

HRID 1774847 reaction equation
[C:1]([NH2:5])(=[O:4])[CH2:2][CH3:3].[H-].[Na+].[Br:8][C:9]1[CH:10]=[N:11][CH:12]=[C:13]([CH2:15]Cl)[CH:14]=1.O>CN(C=O)C>[Br:8][C:9]1[CH:14]=[C:13]([CH2:15][NH:5][C:1](=[O:4])[CH2:2][CH3:3])[CH:12]=[N:11][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6578PropionamideHCID 24758Sodium hydrideHCID 117012593-Bromo-5-(chloromethyl)pyridine

Product 1

HCID 86679194N-(5-Bromo-pyridin-3-ylmethyl)-propionamideYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of propionamide (146 mg, 2.0 mmol) in DMF (10 mL) was added NaH (61 mg, 2.4 mmol) at 0° C. and reaction mixture was stirred for 10 min before the addition of 3-bromo-5-chloromethyl-pyridine (intermediate A-12 [A], 412 mg, 2.0 mmol). The resulting reaction mixture was stirred at room temperature for 1 hour before water was added. Then, the reaction mixture was extracted with EtOAc and combined organic layers were dried by anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was then purified by flash chromatography to give title compound (400 mg, 82%) as a solid.

Workup

  1. customreaction mixture
  2. customThe resulting reaction mixture
  3. additionwas added
  4. extractionThen, the reaction mixture was extracted with EtOAc
  5. dry with materialwere dried by anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was then purified by flash chromatography

Sources & evidence

ORD record
ord-6590dc14b5fd4d96afcad238d67eff05
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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