Sodium Carbonate → HCID 22734164, compound

HRID 1057909Notes

Reaction equation

HRID 1057909 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[O:9][CH2:10][CH2:11][O:12][C:7]=2[C:6]([Sn](CCCC)(CCCC)CCCC)=[CH:5][CH:4]=1.I[C:27]1[CH:37]=[CH:36][C:30]([C:31]([O:33][CH2:34][CH3:35])=[O:32])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Na+].[Na+].[F-].[NH4+]>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)C>[CH2:34]([O:33][C:31]([C:30]1[CH:36]=[CH:37][C:27]([C:6]2[C:7]3[O:12][CH2:11][CH2:10][O:9][C:8]=3[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:28][CH:29]=1)=[O:32])[CH3:35]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 25516Ammonium fluorideHCID 142891Ethyl 4-iodobenzoateHCID 22734375HCID 22734375, compound

Product 1

HCID 22734164HCID 22734164, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Compound 187a (0.93 g) obtained in Step A, ethyl 4-iodobenzoate (0.34 ml), palladium acetate (0.05 g), and sodium carbonate (0.54 g) were dissolved in DMF (10 ml), followed by stirring for 6 hours at 60° C. The reaction solution was mixed with an aqueous ammonium fluoride solution and diethyl ether, and then, filtered with Celite. The organic layer was extracted from the resultant, washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate anhydride, and evaporated under reduced pressure for removing the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give Compound 187 (0.30 g, 50%) as colorless crystals.

Workup

  1. filtrationfiltered with Celite
  2. extractionThe organic layer was extracted from the resultant
  3. washwashed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over magnesium sulfate anhydride
  5. customevaporated under reduced pressure
  6. customfor removing the solvent
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-d40ee132181e4be1a3a1e1bd271b45ba
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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