1-Bromo-2-methylpropane → 4-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamide

HRID 594106Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 594106
C(N=C(N(C)C)N(C)C)(C)(C)C.Br[CH2:14][CH:15]([CH3:17])[CH3:16].[F:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=2)(=[O:27])=[O:26])=[CH:21][CH:20]=1>C(#N)C>[F:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([N:28]([CH2:14][CH:15]([CH3:17])[CH3:16])[C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([O:35][CH3:36])[N:30]=2)(=[O:27])=[O:26])=[CH:23][CH:24]=1

Komponenten

5

Edukt 3

HCID 65551-Bromo-2-methylpropaneHCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 898760604-fluoro-N-(6-methoxypyridin-2-yl)benzenesulfonamide

Produkt 1

HCID 898763574-fluoro-N-isobutyl-N-(6-methoxypyridin-2-yl)benzenesulfonamideAusbeute 63,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 2-(tert-butyl)-1,1,3,3-tetramethylguanidine (0.121 ml, 0.581 mmol), 1-bromo-2-methylpropane (0.126 ml, 1.162 mmol) and 4-fluoro-N-(6-methoxypyridin-2-yl)benzenesulfonamide (164 mg, 0.581 mmol) was prepared and dissolved in acetonitrile (4 mL). The reaction was heated by microwaves to 150° C. for 30 minutes, then again for a further 15 minutes. After cooling the reaction was quenched with sodium hydroxide in ethanol and concentrated in vacuo. The product was extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid. The organic phase was dried by passing through a hydrophobic frit, concentrated in vacuo and purified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient), to give the title compound (125.5 mg). LCMS (2 min, formic) Rt 1.33 min, m/z (ES+) 339 (M+H).

Aufarbeitung

  1. customwas prepared
  2. temperatureAfter cooling the reaction
  3. customwas quenched with sodium hydroxide in ethanol
  4. concentrationconcentrated in vacuo
  5. extractionThe product was extracted to the organic phase of an acidic work up between ethyl acetate and 5% citric acid
  6. customThe organic phase was dried
  7. concentrationconcentrated in vacuo
  8. custompurified by flash silica (Si) chromatography (0-25% ethyl acetate-cyclohexane gradient)

Quellen und Nachweise

ORD-Eintrag
ord-3f58bd877713435fa7f3c4434428414a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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