Water → Methyl 5-chloro-2-{[(5-chloropyridin-2-yl)(methyl)amino]methyl}benzoate

HRID 660243Notes

Reaction equation

HRID 660243 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH3:11])=[N:8][CH:9]=1.Br[CH2:13][C:14]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17].O>O1CCCC1>[Cl:24][C:21]1[CH:22]=[CH:23][C:14]([CH2:13][N:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][N:8]=2)[CH3:11])=[C:15]([CH:20]=1)[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 38370245-chloro-N-methylpyridin-2-amineHCID 51358462Methyl 2-(bromomethyl)-5-chlorobenzoate

Product 1

HCID 68863503Methyl 5-chloro-2-{[(5-chloropyridin-2-yl)(methyl)amino]methyl}benzoateYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (60% dispersion in mineral oil, 46 mg, 1.1 mmol) in tetrahydrofuran (4 ml) was added 5-chloro-N-methylpyridin-2-amine (128 mg, 1.14 mmol) in tetrahydrofuran (5 ml) at room temperature and stirred for 30 min. The mixture was added methyl 2-(bromomethyl)-5-chlorobenzoate (250 mg, 0.95 mmol) in tetrahydrofuran (5 ml) at room temperature and stirred at 80° C. for 8 hr. After cooling to room temperature, the mixture was added water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and evaporated. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (10/1) to afford 102 mg (33%) of the title compound:

Workup

  1. stirringstirred at 80° C. for 8 hr
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified
  6. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (10/1)

Sources & evidence

ORD record
ord-d24b75f7bae64f8daea258e9d4df911d
Source dataset
uspto-grants-2011_12
Patent number
US08084476B2

Reaction notes

Loading…