Dimethylformamide → HCID 86588664, compound

HRID 2119652Notes

Reaction equation

HRID 2119652 reaction equation
Cl[C:2]1[C:11]2[CH:10]=[C:9](Br)[CH:8]=[CH:7][C:6]=2[N:5]=[C:4]2[CH:13]=[N:14][N:15]([CH3:16])[C:3]=12.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19].C(N(CC)CC)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.CN(C)C=[O:56]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:16][N:15]1[C:3]2[C:2](=[O:56])[C:11]3[CH:10]=[C:9](/[CH:19]=[CH:18]/[C:17]([O:21][CH2:22][CH3:23])=[O:20])[CH:8]=[CH:7][C:6]=3[NH:5][C:4]=2[CH:13]=[N:14]1

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 23442366HCID 23442366, compound

Product 1

HCID 86588664HCID 86588664, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
120 °C

Procedure

A mixture of 9-chloro-7-bromo-1-methyl-1H-pyrazolo[4,3-b]quinoline (EXAMPLE 19, step 2, 1 g, 3.4 mmol), ethyl acrylate (0.42 ml, 3.9 mmol), triethylamine (0.53 ml, 3.8 mmol), palladium acetate (76 mg, 0.34 mmol) and tri-o-tolylphosphine (0.62 g, 2.0 mmol) in N,N-dimethylformamide (80 ml) was stirred at 120° C. for 7 h. The mixture was cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated, diluted with ethyl acetate (50 ml) and washed with saturated aqueous sodium bicarbonate (50 ml). The water layer was extracted with ethyl acetate (50 ml×2) and the organic layers were combined. After dryness over sodium sulfate and evaporation, the residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (1:3) to afford 0.79 g (74%) of the title compound as a pale yellow solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with ethyl acetate (50 ml)
  5. washwashed with saturated aqueous sodium bicarbonate (50 ml)
  6. extractionThe water layer was extracted with ethyl acetate (50 ml×2)
  7. customAfter dryness over sodium sulfate and evaporation
  8. customthe residue was purified by column chromatography on silica gel eluting with ethyl acetate/hexane (1:3)

Sources & evidence

ORD record
ord-9d22fcd7d6064c17a72447342fe80c5f
Source dataset
uspto-grants-2004_02
Patent number
US06686373B2

Reaction notes

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