Cesium carbonate → HCID 86668064, compound

HRID 538353Notes

Reaction equation

HRID 538353 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:9]2([CH2:16][F:17])[NH:14][C:13](=[O:15])[CH2:12][O:11][CH2:10]2)[C:5]([Cl:8])=[N:6][CH:7]=1.[C:18](=[NH:31])([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>C1(C)C=CC=CC=1.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]>[C:18](=[N:31][C:2]1[CH:3]=[C:4]([C:9]2([CH2:16][F:17])[NH:14][C:13](=[O:15])[CH2:12][O:11][CH2:10]2)[C:5]([Cl:8])=[N:6][CH:7]=1)([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 136809Benzophenone imineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86668063HCID 86668063, compound

Product 1

HCID 86668064HCID 86668064, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5-(5-bromo-2-chloro-pyridin-3-yl)-5-fluoromethyl-morpholin-3-one (199 mg, 0.615 mmol), benzophenone imine (86 mg, 0.473) and Cs2CO3 (620 mg, 1.89 mmol) in toluene (4.6 ml) and dioxane (4.6 ml) was added Pd2(dba)3 (22 mg, 0.024 mmol) and Xantphos (41 mg, 0.071 mmol) and the mixture was purged with nitrogen, the reaction mixture was heated to 100° C. for 4 h. After cooling to 0° C. water was added and the mixture was extracted with EtOAc, the combined organic layers were washed with water, dried with Na2SO4 and evaporated. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4) to provide the title compound as yellowish foam.

Workup

  1. customthe mixture was purged with nitrogen
  2. temperatureAfter cooling to 0° C. water
  3. additionwas added
  4. extractionthe mixture was extracted with EtOAc
  5. washthe combined organic layers were washed with water
  6. dry with materialdried with Na2SO4
  7. customevaporated
  8. customThe residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:4)

Sources & evidence

ORD record
ord-c758ca3fa41b4927bb0a2d35967d25ad
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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