18-Crown-6 → Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

HRID 394212Notes

Reaction equation

HRID 394212 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16](I)[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:27])[N:13]2[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26].[CH2:28]1[O:45][CH2:44]COCCOCCOCCOCCOC1.CC(C)([O-:49])C.[Na+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C)CCN1CCNCC1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:17]=[C:16]([C:28]([O:45][CH3:44])=[O:49])[CH:15]=[C:14]2[C:9]=1[CH:10]=[CH:11][C:12](=[O:27])[N:13]2[C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:26]

Participants

8

Reactant 5

HCID 2855718-Crown-6HCID 634876Binap, (A+-)-HCID 27362291-(2-(Dimethylamino)ethyl)piperazineHCID 226480965-(2-Chlorophenyl)-1-(2,6-dichlorophenyl)-7-iodoquinolin-2(1h)-oneHCID 23676156Sodium t-butoxide

Product 1

HCID 22648161Methyl 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-2-oxo-1,2-dihydroquinoline-7-carboxylate

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To the 5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-7-iodoquinolin-2(1H)-one (48 mg) in an oven-dried flask was added 18-crown-6 (34 mg), sodium t-butoxide (13 mg), tris(dibenzylideneacetone)dipalladium (0) (8.3 mg) and rac-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (17 mg) and the flask carefully filled with argon. The N,N-dimethyl-N-(2-piperazin-1-ylethyl)amine (17 mg) and THF (2 mL) were then added and the reaction stirred at rt for 16 h. The reaction mixture was then filtered and concentrated and the residue purified by reverse phase HPLC to yield the title compound. 1H NMR (500 Hz, CDCl3): δ 7.62-7.35 (m, 8H); 6.74 (d, J=2.3 Hz, 1H); 6.49 (d, J=9.8 Hz, 1H); 5.86 (d, J=2.1 Hz, 1H); 3.16 (t, J=4.8 Hz, 4H); 2.57 (t, J=5.1 Hz, 4H); 2.53-2.46 (m, 4H), 2.28 (s, 6H). Mass spectrum: m/z 557 (M+H).

Workup

  1. additionthe flask carefully filled with argon
  2. filtrationThe reaction mixture was then filtered
  3. concentrationconcentrated
  4. customthe residue purified by reverse phase HPLC

Sources & evidence

ORD record
ord-be3fac605a0948e789ea81bbc3bf0b92
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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