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Ethyl Acetate → N-[5-phenyl-6-chloro 1-[(2-trimethylsilylethoxy)methyl]indazol-3-yl]butanamide

HRID 497648
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 497648
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[Na+].[Na+].Br[C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][C:25]=1[Cl:26])[N:22]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[N:21]=[C:20]2[NH:35][C:36](=[O:40])[CH2:37][CH2:38][CH3:39].C(OCC)(=O)C>O.O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]1([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][C:25]=2[Cl:26])[N:22]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:33])([CH3:34])[CH3:32])[N:21]=[C:20]3[NH:35][C:36](=[O:40])[CH2:37][CH2:38][CH3:39])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
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Komponenten

8

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 22319528N-[5-bromo-6-chloro-1-[(2-trimethylsilylethoxy)methyl]indazol-3-yl]butanamide

Produkt 1

HCID 22319494N-[5-phenyl-6-chloro 1-[(2-trimethylsilylethoxy)methyl]indazol-3-yl]butanamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysator
HCID 962WaterLösungsmittel2×
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

821 mg of phenylboronic acid, 1.14 g of sodium carbonate in 30 cm3 of distilled water and finally 347 mg of tetrakis(triphenylphosphine)palladium are added to 2 g of N-[5-bromo-6-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described in Example 58, in 180 cm3 of dioxane. The mixture is refluxed for 90 minutes and is then allowed to return to 20° C. to add 100 cm3 of ethyl acetate and 100 cm3 of distilled water. The organic phase is washed with 100 cm3 of saturated aqueous sodium chloride solution and then separated out after settling of the phases has taken place and dried over magnesium sulphate. After filtration, the filtrate is concentrated to dryness under reduced pressure (2 kPa; 50° C.) and the residue is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). After drying (90 Pa; 45° C.), 2 g of N-[5-phenyl-6-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide are thus obtained in the form of a yellow oil.

Aufarbeitung

  1. temperatureThe mixture is refluxed for 90 minutes
  2. customto return to 20° C.
  3. washThe organic phase is washed with 100 cm3 of saturated aqueous sodium chloride solution
  4. customseparated out
  5. dry with materialdried over magnesium sulphate
  6. filtrationAfter filtration
  7. concentrationthe filtrate is concentrated to dryness under reduced pressure (2 kPa; 50° C.)
  8. customthe residue is purified by chromatography under an argon pressure of 50 kPa
  9. washon a column of silica gel (particle size 40-60 μm; diameter 4.5 cm), eluting with a cyclohexane/ethyl acetate mixture (80/20 by volume)
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. dry with materialAfter drying (90 Pa; 45° C.), 2 g of N-[5-phenyl-6-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide
  13. customare thus obtained in the form of a yellow oil

Quellen und Nachweise

ORD-Eintrag
ord-db40902044cf41d88f784a425b7ac47d
Quelldatensatz
uspto-grants-2005_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06949579B2

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