Methyl 5-bromo-2-hydroxy-4-methylbenzoate → Methyl 5-((6-chloropyridin-3-yl)methyl)-2-hydroxy-4-methylbenzoate

HRID 629335Notes

Reaction equation

HRID 629335 reaction equation
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

Participants

5

Reactant 2

HCID 11425090Methyl 5-bromo-2-hydroxy-4-methylbenzoateHCID 178420678HCID 178420678, compound

Product 1

HCID 118468445Methyl 5-((6-chloropyridin-3-yl)methyl)-2-hydroxy-4-methylbenzoate

Reagents, catalysts & solvents 2

HCID 178418851HCID 178418851, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-9c5868984bbc405bbab8aa103df14754
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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