Potassium Carbonate → Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

HRID 1760994Notes

Reaction equation

HRID 1760994 reaction equation
[CH2:1](B(O)O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].[Li+].Br[C:15]1[CH:16]=[C:17]([CH:22]=[C:23]([C:25]([N:27]([CH2:31][CH2:32][CH3:33])[CH2:28][CH2:29][CH3:30])=[O:26])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19]>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:28]([N:27]([CH2:31][CH2:32][CH3:33])[C:25]([C:23]1[CH:22]=[C:17]([CH:16]=[C:15]([CH2:1][CH3:2])[CH:24]=1)[C:18]([O:20][CH3:21])=[O:19])=[O:26])[CH2:29][CH3:30]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 433294Lithium ChlorideHCID 521157Ethylboronic acidHCID 21939662Methyl 3-bromo-5-(dipropylcarbamoyl)benzoate

Product 1

HCID 22593628Methyl 3-((dipropylamino)carbonyl]-5-ethylbenzoate

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Ethylboronic acid (0.800 g, 10.8 mmol), dichlorobis(triphenylphosphine)-palladium(II) (0.252 g, 0.360 mmol), potassium carbonate (2.50 g, 18.0 mmol) and lithium chloride (0.151 g, 3.60 mmol) are added to a mixture of methyl 3-bromo-5-[(dipropylamino)carbonyl]benzoate (1.23 g, 3.60 mmol) in dry DMF (20 mL). The mixture is heated at 100 degrees C. for 18 hours. The mixture is then partitioned between ethyl acetate and water. The phases are separated and the ethyl acetate phase is washed with saline, dried over sodium sulfate and concentrated. The concentrate is column chromatographed (silica gel; ethyl acetate/hexanes, 15/85) to give the title compound, MS (ESI+) for C17H25NO3 m/z (M+H)+=292.2.

Workup

  1. customThe mixture is then partitioned between ethyl acetate and water
  2. customThe phases are separated
  3. washthe ethyl acetate phase is washed with saline
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customchromatographed (silica gel; ethyl acetate/hexanes, 15/85)

Sources & evidence

ORD record
ord-120bedf5c11d4e40ba86fd971c0fd1ac
Source dataset
uspto-grants-2005_01
Patent number
US06846813B2

Reaction notes

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