Iodoethane → 5-Bromo-6-ethoxy-N-methoxy-N-methyl-nicotinamide

HRID 82267Notes

Reaction equation

HRID 82267 reaction equation
[Br:1][C:2]1[C:3]([OH:14])=[N:4][CH:5]=[C:6]([CH:13]=1)[C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8].[CH2:15](I)[CH3:16]>C(Cl)Cl.C(=O)([O-])[O-].[Ag+2]>[Br:1][C:2]1[C:3]([O:14][CH2:15][CH3:16])=[N:4][CH:5]=[C:6]([CH:13]=1)[C:7]([N:9]([O:11][CH3:12])[CH3:10])=[O:8]

Participants

5

Reactant 2

HCID 6340IodoethaneHCID 178502683HCID 178502683, compound

Product 1

HCID 866721225-Bromo-6-ethoxy-N-methoxy-N-methyl-nicotinamideYield 30%

Reagents, catalysts & solvents 2

HCID 178418647HCID 178418647, compoundCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-bromo-6-hydroxy-N-methoxy-N-methyl-nicotinamide (Preparation 239, 1.80 g, 6.90 mmol), ethyl iodide (2.8 mL, 34.5 mmol) and silver carbonate (3.8 g, 13.8 mmol) in DCM (10 mL) was stirred at room temperature for 40 hours. The reaction mixture was diluted with DCM (50 mL), washed with water (2×30 mL), brine (20 mL), dried (Na2SO4) and evaporated in vacuo. The crude material was purified by column chromatography on silica gel (EtOAc:petroleum ether 2:5) to afford the title compound as a yellow sticky solid in 30% yield, 600 mg.

Workup

  1. washwashed with water (2×30 mL), brine (20 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe crude material was purified by column chromatography on silica gel (EtOAc:petroleum ether 2:5)

Sources & evidence

ORD record
ord-f386813016b74239a678ab6da7fa1ccf
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Reaction notes

Loading…