Potassium Phosphate, Tribasic → 1,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate

HRID 662058Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 662058
Br[C:2]1[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:26][C:27]([Si:30]([CH3:43])([CH3:42])[O:31][CH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)([CH3:29])[CH3:28]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2CCCCC2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2OC)CCCCC1>[CH3:29][C:27]([Si:30]([CH3:43])([CH3:42])[O:31][CH2:32][C:33]1[CH:34]=[C:35]([C:2]2[CH:3]=[CH:4][C:5]([CH3:17])=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=2)[CH:36]=[CH:37][CH:38]=1)([CH3:26])[CH3:28]

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 57813315tert-butyl N-[(5-bromo-2-methylphenyl)methyl]carbamateHCID 57813382[3-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid

Produkt 1

HCID 578134201,1-Dimethylethyl {[3'-({[(1,1-dimethylethyl)(dimethyl)silyl]-oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamateAusbeute 90,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 16079156(1R)-Dicyclohexyl(2'-methoxy-[1,1'-binaphthalen]-2-yl)phosphaneKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

1,1-Dimethylethyl [(5-bromo-2-methylphenyl)methyl]carbamate (2.7 g, 9.0 mmol), Pd(OAc)2 (81 mg, 0.36 mmol), dicyclohexyl [2′-(methyloxy)-1,1′-binaphthalen-2-yl]phosphane (216 mg, 0.45 mmol) and K3PO4 (2.5 g, 11.7 mmol) were dissolved in dioxane (50 mL). The mixture was heated at 80° C. for 30 min, and then [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (3.1 g, 11.7 mmol) was added. The mixture reaction was stirred at reflux for two days. The solvent was removed under reduced pressure, then diluted with CH2Cl2 (100 mL). The organic layer was washed with water (30 mL), brine (30 mL), and dried over Na2SO4. After removing the solvent, 3.6 g of the crude product 1,1-dimethylethyl {[3′-({[(1,1-dimethylethyl)-(dimethyl)silyl]oxy}methyl)-4-methyl-3-biphenylyl]methyl}carbamate was obtained (yield: 90%).

Aufarbeitung

  1. customThe mixture reaction
  2. temperatureat reflux for two days
  3. customThe solvent was removed under reduced pressure
  4. additiondiluted with CH2Cl2 (100 mL)
  5. washThe organic layer was washed with water (30 mL), brine (30 mL)
  6. dry with materialdried over Na2SO4
  7. customAfter removing the solvent

Quellen und Nachweise

ORD-Eintrag
ord-54527e44b1fc487abbce59e54699379c
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084449B2

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