Potassium Carbonate → HCID 6432544, compound

HRID 459247Notes

Reaction equation

HRID 459247 reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1)CCC.C([O-])([O-])=O.[K+].[K+].[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30](Cl)=[O:31]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([C:6]1[CH:7]=[CH:8][C:9]([OH:12])=[CH:10][CH:11]=1)=[O:31]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 691102-Chlorobenzoyl chlorideHCID 18443697HCID 18443697, compound

Product 1

HCID 6432544HCID 6432544, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Tributylstannanyl-phenol linked to Wang's resin from Step A (1 eq), Pd2(dba)3 (0.3 eq) and K2CO3 (70 mg) were suspended in THF/Diisopropilmethylamine. To this mixture 2-chloro-benzoyl chloride was added and stirred for 2 hours. The suspension was filtered and the resin washed with MeOH/CH2Cl2/DMF, then HCl diluted/dioxane and Na2CO3 5%(dioxane) and DMF/MeOH/CH2Cl2. Once the resin was dried TFA 95% and CH2Cl2 were added and the mixture stirred at room temperature for 30 min. The resin was filtered and washed with MeOH/CH2Cl2. The solvents were collected and concentrated to dryness to give the title product.

Workup

  1. filtrationThe suspension was filtered
  2. washthe resin washed with MeOH/CH2Cl2/DMF
  3. additionHCl diluted/dioxane and Na2CO3 5%(dioxane) and DMF/MeOH/CH2Cl2
  4. additionwere added
  5. stirringthe mixture stirred at room temperature for 30 min
  6. filtrationThe resin was filtered
  7. washwashed with MeOH/CH2Cl2
  8. customThe solvents were collected
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-055cc3050609493793a21885eb1e9a52
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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