HCID 22100363, compound → HCID 22100408, compound

HRID 1457783Notes

Reaction equation

HRID 1457783 reaction equation
Br[C:2]1[CH:3]=[C:4]2[N:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH3:16])[N:10]([CH2:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]2=[N:6][C:7]=1[CH2:8][OH:9]>C1(C)C=CC=CC=1>[CH2:13]([C:11]1[N:10]([CH2:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2=[N:6][C:7]([CH2:8][OH:9])=[C:2]([C:5]3[CH:4]=[CH:3][CH:2]=[CH:7][N:6]=3)[CH:3]=[C:4]2[N:12]=1)[CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 1

HCID 22100363HCID 22100363, compound

Product 1

HCID 22100408HCID 22100408, compoundYield 141.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 g(0.00249 mole) of the compound obtained in step 7 of Example 1 was dissolved in 10 ml of toluene and to the resulting solution were 1 g(0.00274 mole) of 2-tributyltin pyridine and 0.058 g(0.00005 mole) of tetrakistriphenyl-phosphine palladium. The resultant was refluxed for 24 hours, and cooled to room temperature after the completion of the reaction. The reaction solution was extracted with 100 ml of ethyl acetate and washed with 100 ml of water. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure, and the residue was purified with column chromatography (ethyl acetate) to obtain 0.705 g of the title compound(yield 71%).

Workup

  1. temperatureThe resultant was refluxed for 24 hours
  2. customafter the completion of the reaction
  3. extractionThe reaction solution was extracted with 100 ml of ethyl acetate
  4. washwashed with 100 ml of water
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe residue was purified with column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-f1f671eb3698485ea822d8d09ed0607e
Source dataset
uspto-grants-1998_12
Patent number
US05849753

Reaction notes

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