Cesium carbonate → HCID 57833605, compound

HRID 730070Notes

Reaction equation

HRID 730070 reaction equation
[F:1][C:2]([F:36])([F:35])[C:3]([N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH2:7][C:8](=[C:13]1[C:26]3[CH:25]=[CH:24][CH:23]=[C:22](OS(C(F)(F)F)(=O)=O)[C:21]=3[O:20][C:19]3[C:14]1=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:9]2)=[O:4].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:83](=[NH:96])([C:90]1[CH:95]=[CH:94][CH:93]=[CH:92][CH:91]=1)[C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:83](=[N:96][C:22]1[C:21]2[O:20][C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:13](=[C:8]3[CH2:9][CH:10]4[N:5]([C:3](=[O:4])[C:2]([F:1])([F:35])[F:36])[CH:6]([CH2:12][CH2:11]4)[CH2:7]3)[C:26]=2[CH:25]=[CH:24][CH:23]=1)([C:90]1[CH:91]=[CH:92][CH:93]=[CH:94][CH:95]=1)[C:84]1[CH:89]=[CH:88][CH:87]=[CH:86][CH:85]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 57833591HCID 57833591, compound

Product 1

HCID 57833605HCID 57833605, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 167845palladium(II) acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of trifluoromethanesulfonic acid 9-[8-(2,2,2-trifluoroacetyl)-8-aza-bicyclo[3.2.1]oct-3ylidene]-9H-xanthen-4-yl ester in THF (0.1 to 1 M solution) may be treated with a catalytic amount of a palladium catalyst such as palladium acetate (0.01 to 0.05 equiv), BINAP (0.01 to 0.05 equiv), benzophenone imine (1.05 to 1.5 equiv), and cesium carbonate (1.2 to 2 equiv) under an argon atmosphere. The mixture may be heated to reflux for a period of 10 to 24 hr. After removal of the solvent via evaporation, the residue may be taken up in a halogenated solvent such as methylene chloride, and the solution may be washed with water, dried over a suitable drying agent such as magnesium sulfate, filtered, and concentrated. The residue may be purified via column chromatography to yield Compound 1c.

Workup

  1. temperatureThe mixture may be heated
  2. temperatureto reflux for a period of 10 to 24 hr
  3. customAfter removal of the solvent
  4. customvia evaporation
  5. washthe solution may be washed with water
  6. dry with materialdried over a suitable drying agent such as magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue may be purified via column chromatography

Sources & evidence

ORD record
ord-a34677a130c9463db08276971bb68cf2
Source dataset
uspto-grants-2009_09
Patent number
US07582650B2

Reaction notes

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