Water → HCID 57704605, compound

HRID 1093403Notes

Reaction equation

HRID 1093403 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

Procedure

Compound 51-2 (9.48 g), (5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (7.34 g) synthesized according to the known method (e.g., Tetrahedron vol. 57 (2001) 15 pages 6531-6538), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (868 mg), bis(acetonitrile)palladium(II) dichloride (157 mg) and cesium carbonate (25.6 g) were stirred in acetonitrile (200 ml) at 80° C. for 8 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate, 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. washwashed 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-7c2a512a64ae4ce298f24acbc21766c3
Source dataset
uspto-grants-2012_03
Patent number
US08129361B2

Reaction notes

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