Dabco → HCID 86672978, compound

HRID 467512Notes

Reaction equation

HRID 467512 reaction equation
[N:1]12[CH2:8][CH2:7]N([CH2:5][CH2:6]1)CC2.[C:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17](NC2C=C(C)C(C)=CC=2I)[CH:16]=1)(=[O:12])C=C>CN(C=O)C>[CH3:14][C:15]1[CH:16]=[C:17]2[C:6](=[CH:5][C:20]=1[CH3:19])[NH:1][CH:8]=[C:7]2[C:9]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

4

Reactant 2

HCID 9237DabcoHCID 86672979HCID 86672979, compound

Product 1

HCID 86672978HCID 86672978, compoundYield 140.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

8.60 g of 1,4-diazabicyclo[2.2.2]octane is added to a solution of 25.5 g of the compound obtained in step 1 in 120 ml of DMF. It is degassed with nitrogen, then 0.703 g of palladium acetate is added and the reaction mixture is heated at 120° C. for 7 hours. EtOAc is added, then it is washed with water and with brine, dried over Na2SO4 and evaporated. After trituration of the solid residue with iso ether, 12.3 g of the expected compound is obtained in the form of a beige powder.

Workup

  1. customIt is degassed with nitrogen
  2. addition0.703 g of palladium acetate is added
  3. additionEtOAc is added
  4. washit is washed with water and with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-e14f17833cd84265b3cd4d924e8db8ac
Source dataset
uspto-grants-2014_01
Patent number
US08623862B2

Reaction notes

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