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Potassium Phosphate, Tribasic → N-isobutyl-N-(3-methyl-5-(prop-1-en-2-yl)pyridin-2-yl)-4-((tetrahydro-2H-pyran yl)methoxy)benzenesulfonamide

HRID 594160
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 594160
Cl[C:2]1[CH:3]=[C:4]([CH3:30])[C:5]([N:8]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19]C3CCOCC3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])=[N:6][CH:7]=1.[B-](F)(F)(F)[C:32]([CH3:34])=[CH2:33].[K+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1>[CH2:26]([N:8]([C:5]1[C:4]([CH3:30])=[CH:3][C:2]([C:2]([CH3:3])=[CH2:7])=[CH:7][N:6]=1)[S:9]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH:15]2[CH2:14][CH2:34][CH2:32][CH2:33][O:18]2)=[CH:16][CH:17]=1)(=[O:11])=[O:10])[CH:27]([CH3:28])[CH3:29]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 23670158Potassium (prop-1-en-2-yl)trifluoroborateHCID 72194556N-(5-chloro-3-methylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide

Produkt 1

HCID 117926226N-isobutyl-N-(3-methyl-5-(prop-1-en-2-yl)pyridin-2-yl)-4-((tetrahydro-2H-pyran yl)methoxy)benzenesulfonamideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

N-(5-chloro-3-methylpyridin-2-yl)-N-isobutyl-4-((tetrahydro-2H-pyran-4-yl)methoxy)benzenesulfonamide (140 mg, 0.31 mmol), potassium trifluoro(prop-1-en-2-yl)borate (69 mg, 464 μmol) and Buchwald's Suzuki-Miyaura cross-coupling pre-catalyst (prepared according to ref. J. Am. Chem. Soc. 2010, 132, 14073) (5 mg, 6.18 μmol) were dissolved in anhydrous THF (1 mL). To this solution was added degassed potassium phosphate (0.5 M aqueous) (2 mL, 1.0 mmol) then the reaction vessel sealed and heated by microwaves to 110° C. for 30 minutes. The reaction was cooled, combined with a previous identical trial reaction on a smaller (0.06 mmol) scale and concentrated in vacuo. The crude product was then extracted to the organic phase of an aqueous work up between ethyl acetate and water. The organic phase was passed through a hydrophobic frit, concentrated in vacuo, then purified by mass directed autoprep (formic acid modifier) to give the title compound 85% purity (87 mg). LCMS (2 min, formic) Rt 1.44 min, m/z (ES+) 459 (M+H).

Aufarbeitung

  1. additionTo this solution was added
  2. customthe reaction vessel sealed
  3. temperatureThe reaction was cooled
  4. customcombined with a previous identical trial reaction on a smaller (0.06 mmol) scale
  5. concentrationconcentrated in vacuo
  6. extractionThe crude product was then extracted to the organic phase of an aqueous work up between ethyl acetate and water
  7. concentrationconcentrated in vacuo
  8. custompurified by mass

Quellen und Nachweise

ORD-Eintrag
ord-ed6f3a36d13043c8b662c6419caeb025
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09242972B2

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