Cesium carbonate → HCID 59407737, compound

HRID 1093473Notes

Reaction equation

HRID 1093473 reaction equation
Br[C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:17]([O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1)[C:18]#[CH:19].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[Cl-].[Na+].O.CC#N.CC#N.Cl[Pd]Cl.C(#N)C>[S:4]1[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:2]([C:19]#[C:18][CH2:17][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)=[CH:3]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 123250Benzo(b)thiophene, 3-bromo-HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

Product 1

HCID 59407737HCID 59407737, compound

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 3-bromobenzothiophene(5.00 g), cesium carbonate (20.0 g), 2-(2-propynyloxy)tetrahydropyran (4.96 ml), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (672 mg), bis(acetonitrile)palladium(II) dichloride (122 mg) and acetonitrile (100 ml) was stirred at 90° C. for 11 hr. The reaction mixture was added to brine, 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=99:1-80:20) to give the object product (2.19 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=99:1-80:20)

Sources & evidence

ORD record
ord-c97659c5647d4846aa764234f62104f6
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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