5-Bromo-2-methylamino-nicotinic acid ethyl ester → 5-Ethyl-2-methylamino-nicotinic acid ethyl ester

HRID 2244356Notes

Reaction equation

HRID 2244356 reaction equation
[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9](Br)[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2].[CH2:15]([Zn]CC)[CH3:16]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:14])[C:5]1[CH:10]=[C:9]([CH2:15][CH3:16])[CH:8]=[N:7][C:6]=1[NH:12][CH3:13])[CH3:2]

Participants

4

Reactant 2

HCID 687024045-Bromo-2-methylamino-nicotinic acid ethyl esterHCID 178418750HCID 178418750, compound

Product 1

HCID 687007835-Ethyl-2-methylamino-nicotinic acid ethyl esterYield 15%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 5-bromo-2-methylamino-nicotinic acid ethyl ester (400 mg, 1.54 mmol), diethylzinc solution (1 M in hexane, 3.1 mL, 3.1 mmol), and dichloro[1,1′-bis(diphenylphosphine)ferrocene]palladium(II) (34 mg, 46 μmol) in 1,4-dioxane was heated at reflux for 2 h, then partitioned between ethyl acetate and sat. aq. ammonium chloride solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) afforded the title compound (48 mg, 15%). Colourless liquid, MS (ISP): 209.3 (M+H)+.

Workup

  1. temperatureat reflux for 2 h
  2. custompartitioned between ethyl acetate and sat. aq. ammonium chloride solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-12c3d93762ee48a487f8df9e8734ec18
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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