Cesium carbonate → HCID 67419912, compound

HRID 2406028Notes

Reaction equation

HRID 2406028 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:6]([CH:9]=1)[C:7]#[N:8].[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].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:19]([O:23][C:24](=[O:36])[NH:25][C:26]1([C:34]#[C:35][C:2]2[CH:3]=[CH:4][C:5]([O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[C:6]([C:7]#[N:8])[CH:9]=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 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 115143851,1-Dimethylethyl N-(5-ethynyl-2,2-dimethyl-1,3-dioxan-5-yl)carbamateHCID 18958547HCID 18958547, compound

Product 1

HCID 67419912HCID 67419912, compound

Reagents, catalysts & solvents 3

HCID 6093782Bis(acetonitrile)dichloropalladiumCatalystHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 7-1 (0.636 g), (2,2-dimethyl-5-ethynyl-1,3-dioxan-5-yl)carbamic acid t-butyl ester (0.571 g), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (0.045 g), bis(acetonitrile)palladium(II) dichloride (0.008 g) and cesium carbonate (0.668 g) were stirred in acetonitrile (10 ml) at 70-80° C. for 2 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 [2,2-dimethyl-5-(3-cyano-4-octyloxyphenylethynyl)-1,3-dioxan-5-yl]carbamic acid t-butyl ester as a brown oil. The oil was dissolved in ethyl acetate (6 ml), 10% palladium carbon (about 50% water containing, 0.080 g) was added, and the mixture was stirred at room temperature for 3.5 hr under a hydrogen atmosphere. The solution was filtrated, and the filtrate was concentrated to give the object product (0.610 g) as a pale-yellow powder.

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-de15b23b654042bd9837e083c2a42b2b
Source dataset
uspto-grants-2014_08
Patent number
US08809304B2

Reaction notes

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