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

HRID 657351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657351
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 cooling 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 an Al2O3 column chomatography, eluting with CH2Cl2/CH3OH (300:1). 3′-({[(1,1-Dimethylethyl)(dimethyl)silyl]oxy}methyl)-2-fluoro-3-biphenylcarboxamide, was obtained (4.1 g, yield: 63%). 1H NMR (400 MHz, CDCl3) δ 0.12 (s, 6H), 0.95 (s, 9H), 4.81 (s, 2H), 7.25-8.12 (m, 7H).

Aufarbeitung

  1. temperatureAfter cooling 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 an Al2O3 column chomatography
  8. washeluting with CH2Cl2/CH3OH (300:1)

Quellen und Nachweise

ORD-Eintrag
ord-8f6b07a1492642e1a178505b44044591
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071588B2

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