Potassium Carbonate → HCID 67007161, compound

HRID 564009Notes

Reaction equation

HRID 564009 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7](B(O)O)=[CH:6][CH:5]=1)([OH:3])=[O:2].Br[C:14]1[CH:15]=[C:16]([CH:25]=[CH:26][CH:27]=1)[CH2:17][N:18]1[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([CH2:17][C:16]2[CH:15]=[C:14]([C:7]3[CH:8]=[CH:9][C:4]([C:1]([OH:3])=[O:2])=[CH:5][CH:6]=3)[CH:27]=[CH:26][CH:25]=2)[CH2:19][CH2:20]1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 765903HCID 765903, compound

Product 1

HCID 67007161HCID 67007161, compoundYield 103.6%

Reagents, catalysts & solvents 3

HCID 178420554HCID 178420554, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

98 mg 4-Carboxybenzeneboronic acid, 159 mg 1-(3-Bromo-benzyl)-4-methyl-piperazine, 410 mg potassium carbonate, and 69 mg tetrakis-triphenylphosphino-palladium were stirred under an argon atmosphere in a mixture of 1 ml dioxane and 1 ml water at 85 C for 16 hrs. The mixture was cooled to RT, diluted with 100 ml water and filtered. The filtrate was carefully treated with conc. HCl until the product precipitated. Filtration and drying of the residue yielded 190 mg of the title product.

Workup

  1. filtrationfiltered
  2. additionThe filtrate was carefully treated with conc. HCl until the product
  3. customprecipitated
  4. filtrationFiltration
  5. customdrying of the residue

Sources & evidence

ORD record
ord-275d91fd52a742e3991b7760bee09967
Source dataset
uspto-grants-2011_11
Patent number
US08067599B2

Reaction notes

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