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Triethylamine → 2-(6-chloro-5-fluoro-1-methanesulfonyl-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol

HRID 1182198
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1182198
[Cl:1][C:2]1[C:3]([F:14])=[CH:4][C:5](I)=[C:6]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])[CH:7]=1.C(N(CC)CC)C.[CH2:22]([S:24][CH2:25][C:26]([CH3:30])([OH:29])[C:27]#[CH:28])[CH3:23]>O1CCCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5]([CH:28]=[C:27]([C:26]([OH:29])([CH3:30])[CH2:25][S:24][CH2:22][CH3:23])[N:8]2[S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1[F:14]
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Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 589795961-Ethylsulfanyl-2-methyl-but-3-yn-2-olHCID 66865370N-(5-chloro-4-fluoro-2-iodo-phenyl)-methanesulfonamide

Produkt 1

HCID 115886722-(6-chloro-5-fluoro-1-methanesulfonyl-1H-indol-2-yl)-1-ethylsulfanyl-propan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Katalysator
HCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysator
HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a 50 mL round-bottom flask were added N-(5-chloro-4-fluoro-2-iodo-phenyl)-methanesulfonamide (0.30 g, 1.0 mmol), bis(triphenylphosphine) palladium(II) chloride (35 mg, 0.05 mmol) and copper (I) iodide (19 mg, 0.1 mmol). The flask was fitted with a septum and stirred under argon. Tetrahydrofuran (5 mL) and triethylamine (0.28 mL, 2.0 mmol) were then added via syringe. 1-Ethylsulfanyl-2-methyl-but-3-yn-2-ol (0.14 g, 1.0 mmol) in tetrahydrofuran (1 mL) was added via syringe and the reaction maintained with stirring at 50-60° C. for four hours. The solution was evaporated and the residue purified by column chromatography using dichloromethane as solvent to yield the title compound as a brown oil.

Aufarbeitung

  1. customThe flask was fitted with a septum
  2. temperaturethe reaction maintained
  3. stirringwith stirring at 50-60° C. for four hours
  4. customThe solution was evaporated
  5. customthe residue purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3c2c67169b8941cea09ce41e1cd24328
Quelldatensatz
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07288553B2

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