Cesium carbonate → HCID 57599578, compound

HRID 2356334Notes

Reaction equation

HRID 2356334 reaction equation
CC([N:5]([CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][NH:14][C:13](=[O:17])[CH2:12]1)[C:6](=[O:8])[O-:7])(C)C.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([C:51]2C=CC3[C:53](=CC=CC=3)[C:52]=2[C:61]2C3C(=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:14]1[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][NH:5][C:6](=[O:8])[O:7][C:52]([CH3:61])([CH3:53])[CH3:51])[CH2:12][C:13]1=[O:17]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 112552656-Methoxy-1,5-naphthyridin-4-yl trifluoromethanesulfonateHCID 131728246HCID 131728246, compound

Product 1

HCID 57599578HCID 57599578, compoundYield 887.5%

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-376cdaf3a3a54ba0ac8ae7f407942d3f
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Reaction notes

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