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

HRID 493564Notes

Reaction equation

HRID 493564 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 8028TetrahydrofuranSolvent2×

Procedure

To s suspension of sodium hydride (60% dispersion in mineral oil, 46 mg, 1.1 mmol) in terahydorofuran (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-bef88ad28684470686c5e292a1e3d7e0
Source dataset
uspto-grants-2009_05
Patent number
US07534914B2

Reaction notes

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