Cesium carbonate → HCID 59407634, compound

HRID 1093415Notes

Reaction equation

HRID 1093415 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:18]([O:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[C:19]#[CH:20].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>CC#N.CC#N.Cl[Pd]Cl.O.C(#N)C>[C:7]1(=[O:11])[C:8]2[C:4](=[CH:3][C:2]([C:20]#[C:19][CH2:18][O:21][CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][O:23]3)=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 5206955-Bromo-1-indanoneHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 59407634HCID 59407634, compound

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 5-bromo-1-indanone (10.0 g), cesium carbonate (40.3 g), 2-(2-propynyloxy)tetrahydropyran (10.0 ml), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (1.40 g), bis(acetonitrile)palladium(II) dichloride (246 mg) and acetonitrile (200 ml) was stirred at 90° C. for 6 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-2:1) to give the object product (7.87 g) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1-2:1)

Sources & evidence

ORD record
ord-1fdd617827634ebca9291a3e4002b808
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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