Pyridine → HCID 66700114, compound

HRID 1910721Notes

Reaction equation

HRID 1910721 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]3=2)[C@H:7]([NH2:18])[CH2:6][C@@H:5]1[CH3:19])(=[O:3])[CH3:2].[Cl:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1.N1C=CC=CC=1>CN(C=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]3[CH:17]=[CH:16][CH:15]=[CH:14][C:12]3=2)[C@H:7]([NH:18][C:24]2[CH:25]=[CH:26][C:21]([Cl:20])=[CH:22][CH:23]=2)[CH2:6][C@@H:5]1[CH3:19])(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 742994-Chlorophenylboronic acidHCID 66700019HCID 66700019, compound

Product 1

HCID 66700114HCID 66700114, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

[Step 5] 91 mg of the cis-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydrobenzo[h]quinoline and 84 mg of 4-chlorophenylboronic acid were dissolved in 2.5 mL of DMF followed by adding 130 mg of divalent copper acetate and 87 μL of pyridine and stirring for 30 minutes at room temperature in the presence of air. Following completion of the reaction, the solution was filtered with celite followed by the addition of water and extracting three times with ethyl acetate. After washing with saturated brine and dehydrating with anhydrous sodium sulfate, the solution was concentrated under reduced pressure and the resulting residue was purified using silica gel chromatography (ethyl acetate:hexane=1:1) to obtain 25 mg of the target compound in the form of a yellow solid (19%).

Workup

  1. customcompletion of the reaction
  2. filtrationthe solution was filtered with celite
  3. additionfollowed by the addition of water
  4. extractionextracting three times with ethyl acetate
  5. washAfter washing with saturated brine
  6. concentrationthe solution was concentrated under reduced pressure
  7. customthe resulting residue was purified

Sources & evidence

ORD record
ord-1edaeb4ec52c40a182503e0742126bc6
Source dataset
uspto-grants-2013_12
Patent number
US08604030B2

Reaction notes

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