Cesium carbonate → HCID 10004727, compound

HRID 1987032Notes

Reaction equation

HRID 1987032 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[C:15]2[C:10]([CH:11]=[CH:12][C:13](=[O:24])[N:14]2[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[Cl:31])[CH:8]=1)(=O)=O.[CH:34]([NH:37][CH2:38][CH2:39][NH2:40])([CH3:36])[CH3:35].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:23][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[N:14]1[C:15]2[C:10](=[C:9]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:31])[CH:8]=[C:7]([NH:40][CH2:39][CH2:38][NH:37][CH:34]([CH3:36])[CH3:35])[CH:16]=2)[CH:11]=[CH:12][C:13]1=[O:24]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 88098N-IsopropylethylenediamineHCID 634876Binap, (A+-)-HCID 57722974HCID 57722974, compound

Product 1

HCID 10004727HCID 10004727, compoundYield 11.7%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

1,5-bis(2-chlorophenyl)-2-oxo-1,2-dihydro-7-quinolinyl trifluoromethanesulfonate (50 mg, 0.097 mmol), N-isopropylethylenediamine (0.36 ml, 2.885 mmol), racemic BINAP (74 mg, 0.119 mmol), palladium(II) acetate (17 mg, 0.076 mmol), and cesium carbonate (0.14 g, 0.43 mmol) in 1,4-dioxan (4 ml) were heated under reflux under nitrogen for 2 h. The solvent was removed in vacuo, and the residue partitioned between water (8 ml) and dichloromethane (10 ml). The mixture was passed through a hydrophobic frit, and the filtrate passed though two 5 g SCX-2 cartridges, and eluted with methanol followed by 2M ammonia in methanol. The latter fractions were evaporated in vacuo and the residue purified by mass directed autoprep (per general procedure B) to afford the title compound as a gum (5.3 mg, 10%).

Workup

  1. temperatureunder reflux under nitrogen for 2 h
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between water (8 ml) and dichloromethane (10 ml)
  4. washeluted with methanol
  5. customThe latter fractions were evaporated in vacuo
  6. customthe residue purified by mass

Sources & evidence

ORD record
ord-79dda68ec5834ceba9c9dff66b61a2ce
Source dataset
uspto-grants-2009_06
Patent number
US07550480B2

Reaction notes

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