Pyridine → N-(6-bromo-2,4-dimethylpyridin-3-yl)-3,3-dimethylbutanamide

HRID 383704Notes

Reaction equation

HRID 383704 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH2:9])=[C:4]([CH3:10])[CH:3]=1.N1C=CC=CC=1.[C:17]([CH2:21][C:22](Cl)=[O:23])([CH3:20])([CH3:19])[CH3:18]>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([CH3:8])[C:5]([NH:9][C:22](=[O:23])[CH2:21][C:17]([CH3:20])([CH3:19])[CH3:18])=[C:4]([CH3:10])[CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 815143,3-Dimethylbutanoyl chlorideHCID 288753476-Bromo-2,4-dimethylpyridin-3-amine

Product 1

HCID 59868778N-(6-bromo-2,4-dimethylpyridin-3-yl)-3,3-dimethylbutanamideYield 91.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1c (0.364 g, 1.81 mmol) and pyridine (0.158 ml, 2 mmol) in dichloromethane (5 ml) was added tert-butylacetyl chloride (0.242 g, 1.8 mmol). The mixture was stirred at room temperature for 2 hours. The mixture was washed with brine and extracted with ethyl acetate. The organic layer was dried over MgSO4, concentrated and chromatographed to yield 1d (0.361 g, 1.64 mmol, 91%).

Workup

  1. washThe mixture was washed with brine
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated
  5. customchromatographed

Sources & evidence

ORD record
ord-841d0c1e53d240e3bcf3de1ec705cb10
Source dataset
uspto-grants-2013_02
Patent number
US08367684B2

Reaction notes

Loading…