Sodium Carbonate → 1,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-one

HRID 270685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 270685
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:29])[N:7]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.CC([O-])=O.[K+].Cl[C:54]1[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1(P([Pd-3](Cl)(Cl)(P(C2C=CC=CC=2)C2C=CC=CC=2)[C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[F:28][C:25]([F:27])([F:26])[C:22]1[CH:23]=[CH:24][C:19]([N:7]2[C:6](=[O:29])[C:5]3[C:9](=[CH:10][C:2]([C:54]4[C:59]([C:60]([F:63])([F:62])[F:61])=[CH:58][CH:57]=[CH:56][N:55]=4)=[CH:3][CH:4]=3)[N:8]2[CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:16])[CH3:18])=[CH:20][CH:21]=1

Komponenten

8

Edukt 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 5898332-Chloro-3-(trifluoromethyl)pyridineHCID 2733548Bis(pinacolato)diboraneHCID 692032346-Bromo-1,2-dihydro-2-(4-trifluoromethylphenyl)-1-(2-trimethylsilyl ethoxymethyl)-3H-indazol-3-one

Produkt 1

HCID 866128481,2-Dihydro-2-(4-trifluoromethylphenyl)-6-(3-trifluoromethyl-2-pyridinyl)-1-(2-(trimethylsilyl)ethoxymethyl)-3H-indazol-3-oneAusbeute 13,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178479788HCID 178479788, VerbindungKatalysator2×HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The product of Step 5 (1.3 g, 2.6 mmol), was dissolved in dioxane (10 mL) and flushed with N2. Bis(pinacolato)diboron (680 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (60 mg) and KOAc (380 mg, 3.9 mmol) were added. The mixture was stirred at 100° C. overnight. 2-Chloro-3-trifluoromethylpyridine (470 mg, 2.6 mmol), bis(diphenylphosphino)ferrocenyl palladium(II) dichloride (20 mg) and saturated Na2CO3 solution (1 mL) were added, and the mixture heated at reflux for a further 18 h. Purification by column chromatography gave 0.2 g of product as an oil.

Aufarbeitung

  1. customflushed with N2
  2. temperaturethe mixture heated
  3. temperatureat reflux for a further 18 h
  4. customPurification by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-966c5ef759ed41eaadad4c4e9772a7c0
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449585B2

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