Water → HCID 57704605, compound

HRID 2406045Notes

Reaction equation

HRID 2406045 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12](Br)=[CH:11][C:10]=1[CH:16]([F:18])[F:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([O:23][C:24](=[O:36])[NH:25][C:26]1([C:34]#[CH:35])[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+].O>C(#N)C.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:19]([O:23][C:24](=[O:36])[NH:25][C:26]1([C:34]#[C:35][C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:10]([CH:16]([F:18])[F:17])[CH:11]=2)[CH2:31][O:30][C:29]([CH3:33])([CH3:32])[O:28][CH2:27]1)([CH3:22])([CH3:21])[CH3:20]

Participants

8

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 57704617HCID 57704617, compound

Product 1

HCID 57704605HCID 57704605, compoundYield 79.2%

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

Compound 30-2 (9.48 g), (2,2-dimethyl-5-ethynyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (7.34 g) synthesized by a known method (for example, Tetrahedron vol. 57 (2001) 6531-6538), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (868 mg), bis(acetonitrile)palladium(II) dichloride (157 mg) and cesium carbonate (25.6 g) in acetonitrile (200 ml) were stirred at 80° C. for 8 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 product (11.1 g) as a pale-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-9eb51cd5c90e40c79a423f76984d0dd4
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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