Cesium carbonate → HCID 68929525, compound

HRID 2406050Notes

Reaction equation

HRID 2406050 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH:16]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[C:25]([O:29][C:30](=[O:42])[NH:31][C:32]1([C:40]#[CH:41])[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[O:34][CH2:33]1)([CH3:28])([CH3:27])[CH3:26].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.CC#N.CC#N.Cl[Pd]Cl.O>[C:25]([O:29][C:30](=[O:42])[NH:31][C:32]1([C:40]#[C:41][C:2]2[CH:3]=[CH:4][C:5]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[C:6]([CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:16]=2)[CH2:37][O:36][C:35]([CH3:39])([CH3:38])[O:34][CH2:33]1)([CH3:28])([CH3:27])[CH3:26]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 68929535HCID 68929535, compound

Product 1

HCID 68929525HCID 68929525, compound

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Compound 34-3 (10.5 g), (2,2-dimethyl-5-ethynyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (6.46 g) synthesized by a known method (for example, Tetrahedron vol. 57 (2001) 6531-6538), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (725 mg), bis(acetonitrile)palladium(II) dichloride (131 mg) and cesium carbonate (21.4 g) in acetonitrile (150 ml) was stirred at 80° C. for 12 hr. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to give the object (11.7 g) as a brown oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography
  6. customto give the object (11.7 g) as a brown oil

Sources & evidence

ORD record
ord-d87ed93fac3248d89ab87421a0115413
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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