Potassium Carbonate → HCID 57706053, compound

HRID 1662513Notes

Reaction equation

HRID 1662513 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1I.[C:13]1(B(O)O)=[CH:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O.C1C=CC([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)=CC=1>[C:13]1([C:3]2[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=2[OH:1])[C:6]([O:8][CH3:9])=[O:7])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH:19]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 3434501Cyclohepten-1-ylboronic acidHCID 11346465Methyl 4-hydroxy-3-iodobenzoate

Product 1

HCID 57706053HCID 57706053, compoundYield 44%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 4-hydroxy-3-iodobenzoate (1.4 g, 5.0 mmol) (commercially available from Aldrich) in DMF (15 mL) at 23° C. was added (Z)-cycloheptenylboronic acid (0.74 g, 5.3 mmol, commercially available from Combi-Blocks), potassium carbonate (2.1 g, 15 mmol), followed by tetrakis(triphenylphosphine)palladium (0.58 g, 0.50 mmol). The mixture was heated to 100° C. The reaction was then stirred for 17 hours and then cooled to room temperature. The reaction was diluted with brine and extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-20% EtOAc in hexanes) to yield 78.7A as a colorless oil (0.55 g, 44% yield).

Workup

  1. temperaturecooled to room temperature
  2. extractionextracted three times with EtOAc
  3. dry with materialAfter drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. customthe organic solvent was removed under reduced pressure
  6. customthe product was then purified on silica gel (0-20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-14f33c93291a4ab7b27de14797fef1c3
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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