Triethylamine → HCID 136336853, compound

HRID 69103Notes

Reaction equation

HRID 69103 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:15]([CH:16]4[CH2:20][CH2:19][CH2:18][CH2:17]4)[N:14]=[CH:13][C:7]=3[C:8](=[O:12])[NH:9][C:10]=2[CH:11]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=O.[C:59]([O:62][CH2:63]C)(=[O:61])C>CS(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CO>[CH:16]1([N:15]2[C:6]3[C:5]4[CH:4]=[CH:3][C:2]([C:59]([O:62][CH3:63])=[O:61])=[CH:11][C:10]=4[NH:9][C:8](=[O:12])[C:7]=3[CH:13]=[N:14]2)[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

10

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 812191,3-Bis(diphenylphosphino)propaneHCID 136336852HCID 136336852, compoundHCID 178418416HCID 178418416, compound

Product 1

HCID 136336853HCID 136336853, compound

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 735 mg of 7-bromo-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[4,3-c]quinolin-4-one in 6 mL of dimethylsulfoxide were sequentially added 49 mg of palladium acetate, 91 mg of 1,3-bis(diphenylphosphino)propane, 0.62 mL of triethylamine, and 3 mL of methanol, and the atmosphere in the reaction container was replaced with carbon monoxide. The mixture was stirred at 70° C. for 7 hours, cooled to room temperature, and then poured into a mixture of water and ethyl acetate. The aqueous layer was separated, the organic layer was washed with diluted hydrochloric acid and saturated brine, and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (chloroform/methanol) to obtain 551 mg of methyl 1-cyclopentyl-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]quinoline-7-carboxylate.

Workup

  1. temperaturecooled to room temperature
  2. customThe aqueous layer was separated
  3. washthe organic layer was washed with diluted hydrochloric acid and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-65e89e2a63c949689eb83005048a5f45
Source dataset
uspto-grants-2014_09
Patent number
US08822448B2

Reaction notes

Loading…