Methyl 5-bromo-2-hydroxy-4-methylbenzoate → Methyl 5-((6-chloropyridin-3-yl)methyl)-2-hydroxy-4-methylbenzoate
反応式
Br[C:2]1[C:3]([CH3:13])=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[Cl-].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][Zn+])=[CH:18][N:17]=1.C1COCC1>C1COCC1.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[Cl:15][C:16]1[N:17]=[CH:18][C:19]([CH2:22][C:2]2[C:3]([CH3:13])=[CH:4][C:5]([OH:12])=[C:6]([CH:11]=2)[C:7]([O:9][CH3:10])=[O:8])=[CH:20][CH:21]=1参加物
5
実験手順
To a solution of methyl 5-bromo-2-hydroxy-4-methylbenzoate (0.61 g) in THF (20.0 mL) were added 0.5M (2-chloro-5-pyridyl)methylzinc chloride/THF solution (12.5 mL) and bis(tri-tert-butylphosphine)palladium(0) (0.13 g), and the mixture was stirred overnight at room temperature under argon atmosphere. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.52 g).