Cesium carbonate → HCID 57599578, compound

HRID 1787690Notes

Reaction equation

HRID 1787690 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH2:5][N:4]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:3]1.FC(F)(F)S(O[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([O:34][CH3:35])[N:32]=2)[N:27]=[CH:26][CH:25]=1)(=O)=O.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.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]>[CH3:35][O:34][C:31]1[N:32]=[C:33]2[C:28](=[CH:29][CH:30]=1)[N:27]=[CH:26][CH:25]=[C:24]2[N:7]1[CH2:6][CH2:5][N:4]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:3][C:2]1=[O:1]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonateHCID 57599583HCID 57599583, compound

Product 1

HCID 57599578HCID 57599578, compoundYield 53.2%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

In a sealed tube 1,1-dimethylethyl [2-(3-oxo-1-piperazinyl)ethyl]carbamate (1.7 g, 7.02 mmol), 6-(methyloxy)-1,5-naphthyridin-4-yl trifluoromethanesulfonate (2.17 g, 7.02 mmol), Pd2dba3 (436 mg, 0.421 mmol), rac-Binap (262 mg, 0.421 mmol), Cs2CO3 (4.81 g, 14.75 mmol) and 18-C-6 (186 mg, 0.702 mmol) in dioxane (35 mL) were combined and flushed with N2. After 15 min, the tube was sealed and heated to 100° C. while stirring rapidly. After 12 h, the solution was filtered, concentrated and the residue purified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH)) yielding the title compound (1.5 g, 53%) as a burgundy foam: LCMS (ES) m/e 402 (M+H)+.

Workup

  1. customflushed with N2
  2. customthe tube was sealed
  3. waitAfter 12 h
  4. filtrationthe solution was filtered
  5. concentrationconcentrated
  6. customthe residue purified via column chromatography (silica, 1% MeOH in DCM (1% NH4OH))

Sources & evidence

ORD record
ord-ac53345574d043ea8fa3e9e6e7420625
Source dataset
uspto-grants-2009_03
Patent number
US07511035B2

Reaction notes

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