Dabco → HCID 21087570, compound

HRID 348527Notes

Reaction equation

HRID 348527 reaction equation
O1CCC(=O)C[CH2:2]1.[CH3:8][O:9][C:10](=[O:19])[C:11]1[CH:16]=[CH:15][C:14](N)=[C:13](I)[CH:12]=1.C1[N:25]2[CH2:26][CH2:27][N:22]([CH2:23][CH2:24]2)C1.[O-]S([O-])(=O)=O.[Mg+2]>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:24]1[C:23]2[NH:22][C:12]3[C:11]([C:10]([O:9][CH3:8])=[O:19])=[CH:16][CH2:15][CH2:14][C:13]=3[C:2]=2[CH:27]=[CH:26][NH:25]1

Participants

7

Reactant 4

HCID 9237DabcoHCID 24083Sulfuric acid magnesium salt (1:1)HCID 121599Tetrahydro-4H-pyran-4-oneHCID 4104649Methyl 4-amino-3-iodobenzoate

Product 1

HCID 21087570HCID 21087570, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

Tetrahydro-4H-pyran-4-one (1.3 g, 13 mmol), 4-amino-3-iodobenzoic acid methyl ester (3.46 g, 12.5 mmol), DABCO (4.37 g, 39 mmol), MgSO4 (2.35 g, 19.5 mmol) and Pd(OAc)2 (0.15 g, 0.00065 mol) were dissolved in DMF (18 mL) and heated under nitrogen at 105° C. for 2 days. The reaction mixture was then partitioned between ethyl acetate and water, and extracted. The crude was purified by column chromatography (98/2 DCM/MeOH) to give 0.62 g of title compound.

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. extractionextracted
  3. customThe crude was purified by column chromatography (98/2 DCM/MeOH)

Sources & evidence

ORD record
ord-56e7c2500d1a42abbf674447f1cb4d83
Source dataset
uspto-grants-2007_02
Patent number
US07176322B2

Reaction notes

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