Cesium carbonate → HCID 57704585, compound

HRID 2406054Notes

Reaction equation

HRID 2406054 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][CH2:24][CH3:25])=[C:6]([CH:16]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[C:26]([O:30][C:31](=[O:43])[NH:32][C:33]1([C:41]#[CH:42])[CH2:38][O:37][C:36]([CH3:40])([CH3:39])[O:35][CH2:34]1)([CH3:29])([CH3:28])[CH3:27].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[Cl-].[Na+].O.CC#N.CC#N.Cl[Pd]Cl.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>[C:26]([O:30][C:31](=[O:43])[NH:32][C:33]1([C:41]#[C:42][C:2]2[CH:3]=[CH:4][C:5]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[C:6]([CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:16]=2)[CH2:38][O:37][C:36]([CH3:40])([CH3:39])[O:35][CH2:34]1)([CH3:29])([CH3:28])[CH3:27]

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 57704613HCID 57704613, compound

Product 1

HCID 57704585HCID 57704585, compoundYield 83.5%

Reagents, catalysts & solvents 4

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 6342AcetonitrileSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

Compound 35-3 (11.1 g), (2,2-dimethyl-5-ethynyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (6.28 g) synthesized by a known method (for example, Tetrahedron vol. 57 (2001) 6531-6538), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (706 mg), bis(acetonitrile)palladium(II) dichloride (128 mg) and cesium carbonate (20.8 g) in acetonitrile (150 ml) were stirred at 80° C. for 10 hr. Brine 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 product (12.4 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

Sources & evidence

ORD record
ord-1d410bcb36d146b29fd037967a618af2
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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