Potassium Carbonate → 1-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

HRID 394222Notes

Reaction equation

HRID 394222 reaction equation
BrC1C=C(OC)C=C2C=1CCC(=O)N2C1C(Cl)=CC=CC=1Cl.[H-].[Na+].[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[N:33]1[C:42]2[C:37](=[C:38]([C:45]3[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:46]=3[F:52])[CH:39]=[C:40]([O:43]C)[CH:41]=2)[CH2:36][CH2:35][C:34]1=[O:53].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=1[N:33]1[C:42]2[C:37](=[C:38]([C:45]3[CH:50]=[CH:49][C:48]([F:51])=[CH:47][C:46]=3[F:52])[CH:39]=[C:40]([OH:43])[CH:41]=2)[CH2:36][CH2:35][C:34]1=[O:53]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 226479975-Bromo-1-(2,6-dichlorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinoneHCID 226480981-(2,6-dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-methoxy-2(1H)-quinolinone2×

Product 1

HCID 226480931-(2,6-Dichlorophenyl)-5-(2,4-difluorophenyl)-3,4-dihydro-7-hydroxy-2(1H)-quinolinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of compound 1 (126 mg, 0.3 mmol) and sodium hydride (60%) (12 mg, 0.3 mmol) in 6 mL of DMF was stirred for 1 h at rt. Then the compound 2 (78 mg, 0.33 mmol) was added and stirred for 12 h at 135° C. Potassium carbonate (83 mg, 0.6 mmol) and compound 2 (78 mg, 0.33 mmol) was again added to the reaction mixture and stirred for another 24 h at 135° C. After removal of solvent, it was poured in to 30 mL of ethyl acetate and 10 mL of aq Na2CO3, and it was extracted with ethyl acetate (15 mL×3). The combined organic layer was dried over Na2CO3 and concentrated. After removal of solvent, the residue was purified by TLC with hexane/ethyl acetate/2N NH3 in MeOH to afford compound 3 (white solid). Mass spectrum (ESI) for 3, 555 (M+1) and 557 (M+3).

Workup

  1. stirringstirred for 12 h at 135° C
  2. stirringstirred for another 24 h at 135° C
  3. customAfter removal of solvent, it
  4. additionwas poured in to 30 mL of ethyl acetate and 10 mL of aq Na2CO3, and it
  5. extractionwas extracted with ethyl acetate (15 mL×3)
  6. dry with materialThe combined organic layer was dried over Na2CO3
  7. concentrationconcentrated
  8. customAfter removal of solvent
  9. customthe residue was purified by TLC with hexane/ethyl acetate/2N NH3 in MeOH

Sources & evidence

ORD record
ord-c7b3a30d4a994e32b5125129eac71026
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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