Potassium Carbonate → 3'-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylcarboxamide

HRID 564474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 564474
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+].Br[C:27]1[C:28]([F:36])=[C:29]([CH:33]=[CH:34][CH:35]=1)[C:30]([NH2:32])=[O:31].[CH3:37][C:38]([Si:41]([CH3:54])([CH3:53])[O:42][CH2:43][C:44]1[CH:45]=[C:46](B(O)O)[CH:47]=[CH:48][CH:49]=1)([CH3:40])[CH3:39]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:40][C:38]([Si:41]([CH3:54])([CH3:53])[O:42][CH2:43][C:44]1[CH:45]=[C:46]([C:27]2[CH:35]=[CH:34][CH:33]=[C:29]([C:30]([NH2:32])=[O:31])[C:28]=2[F:36])[CH:47]=[CH:48][CH:49]=1)([CH3:37])[CH3:39]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 442031023-Bromo-2-fluorobenzamideHCID 57813382[3-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid

Produkt 1

HCID 578133053'-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylcarboxamideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Pd(OAc)2 (123.6 mg, 0.55 mmol), PPh3 (557.5 mg, 2.2 mmol), K2CO3 (3.8 g, 27.5 mmol) and 3-bromo-2-fluorobenzamide (4.0 g, 18.4 mmol) were suspended in 1,4-dioxane (30 mL). After the mixture was heated to 80° C. for 15 min, [3-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (5.9 g, 22.0 mmol) was added. Then the reaction mixture was stirred over night at 100° C. After cooled to room temperature, the solvent was removed under reduced pressure. The residue was dissolved in CH2Cl2 (50 mL), then was washed with water (20 mL), brine (20 mL), and dried over Na2SO4. After the solvent was removed, the crude product was purified on Al2O3 column chromatography, eluting with CH2Cl2/CH3OH (300:1). 4.1 g of the product, 3′-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylcarboxamide, was obtained (yield: 63%). 1H NMR (400 MHz, CDCl3): δ 0.12 (s, 6 H), 0.95 (s, 9 H), 4.81 (s, 2 H), 7.25-8.12 (m, 7 H).

Aufarbeitung

  1. temperatureAfter cooled to room temperature
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (50 mL)
  4. washwas washed with water (20 mL), brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. customAfter the solvent was removed
  7. customthe crude product was purified on Al2O3 column chromatography
  8. washeluting with CH2Cl2/CH3OH (300:1)

Quellen und Nachweise

ORD-Eintrag
ord-f10d73e18ac842f0b9ffca8733d982a9
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08067408B2

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