Potassium Carbonate → HCID 69207637, compound

HRID 2251321Notes

Reaction equation

HRID 2251321 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([NH:22][CH3:23])=[C:18]([CH3:24])[CH:17]=2)=[C:12]([CH:25]([CH3:27])[CH3:26])[O:11][N:10]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][C:36]1[CH:37]=[C:38]([CH:43]=[CH:44][CH:45]=1)[C:39]([O:41][CH3:42])=[O:40]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([N:22]([CH2:35][C:36]3[CH:37]=[C:38]([CH:43]=[CH:44][CH:45]=3)[C:39]([O:41][CH3:42])=[O:40])[CH3:23])=[C:18]([CH3:24])[CH:17]=2)=[C:12]([CH:25]([CH3:27])[CH3:26])[O:11][N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 69210775HCID 69210775, compound

Product 1

HCID 69207637HCID 69207637, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of N-(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)-N-methylamine (0.45 g, 1.1 mmol) in dimethylformamide (4 mL) was treated with potassium carbonate (0.15 g, 1.1 mmol) followed by methyl 3-(bromomethyl)benzoate (0.25 g, 1.1 mmol). After stirring at ambient temperature for 24 h, the reaction was partitioned with ethyl acetate and water. The organic layer was washed with water (2×50 mL), brine (50 mL), dried over anhydrous magnesium sulfate, filtered and condensed to a residue which was chromatographed on silica gel eluting with 20% ethyl acetate/hexanes. Yield=0.43 g. (70%) of methyl 3-{[(4-{[3-(2,6-dichlorophenyl)-5-isopropylisoxazol-4-yl]methoxy}-2-methylphenyl)(methyl)-amino]methyl}benzoate.

Workup

  1. customthe reaction was partitioned with ethyl acetate and water
  2. washThe organic layer was washed with water (2×50 mL), brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customcondensed to a residue which
  6. customwas chromatographed on silica gel eluting with 20% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-9e0ffbffec2c4e00b65425cca375b9a9
Source dataset
uspto-grants-2008_01
Patent number
US07319109B2

Reaction notes

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