Potassium Carbonate → HCID 59377985, compound

HRID 2065740Notes

Reaction equation

HRID 2065740 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:11]1[CH:16]=[C:15]([NH2:17])[C:14](Br)=[CH:13][C:12]=1[Cl:19])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[C:21](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([C:11]1[CH:16]=[C:15]([NH2:17])[C:14]([CH3:21])=[CH:13][C:12]=1[Cl:19])[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 59377970HCID 59377970, compound

Product 1

HCID 59377985HCID 59377985, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2-(5-amino-4-bromo-2-chloro-phenyl)-malonic acid diethyl ester (1.25 g, 3.43 mmol) in dioxane (20 ml) and water (2 ml) was added potassium carbonate (1.42 g, 10.28 mmol), PdCl2(dppf) (0.28 g, 0.342 mmol) and trimethyl boroxine (0501 ml, 3.42 mmol). The mixture was stirred at 110° C. for 18 hours, then cooled to room temperature and filtered. The filtrate was concentrated to dryness under reduced pressure. Purification of the crude product by flash chromatography (hexanes:EtOAc 8:2) gave 0.270 g (71%) of 2-(5-amino-2-chloro-4-methyl-phenyl)-malonic acid diethyl ester as a yellow oil.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated to dryness under reduced pressure
  4. customPurification of the crude product by flash chromatography (hexanes:EtOAc 8:2)

Sources & evidence

ORD record
ord-b3958ef4471c47b98ce2e9a34ff9e108
Source dataset
uspto-grants-2012_10
Patent number
US08288552B2

Reaction notes

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