5-Bromo-2-methylamino-nicotinic acid ethyl ester → 5-Ethyl-2-methylamino-nicotinic acid ethyl ester
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
Product 1
Reagents, catalysts & solvents 1
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)+.