Acetonitrile → 4-fluoro-N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)benzenesulfonamide

HRID 594120

Reaktionsgleichung

Reaktionsgleichung von HRID 594120
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:21][CH:22]([CH3:26])[CH:23](O)[CH3:24].C(#N)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([CH3:20])[CH3:19])=[CH:14][N:13]=2)[CH:23]([CH:22]([CH3:26])[CH3:21])[CH3:24])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 6342AcetonitrileHCID 117323-Methyl-2-butanolHCID 89875926HCID 89875926, Verbindung

Produkt 1

HCID 898762524-fluoro-N-(5-isopropylpyridin-2-yl)-N-(3-methylbutan-2-yl)benzenesulfonamideAusbeute 12,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of 4-fluoro-N-(5-isopropylpyridin-2-yl)benzenesulfonamide (203 mg, 0.690 mmol) and 3-methylbutan-2-ol (60.8 mg, 0.690 mmol) in toluene (3 mL) stirred in air at room temperature was added a solution of 2-tributylphosphoranylidene)acetonitrile (166 mg, 0.690 mmol) in toluene (0.5 mL). The reaction vessel was sealed and heated by microwaves to 150° C. for 30 minutes. After cooling, the solvent was evaporated in vacuo and the crude purified by mass directed autoprep (formic acid modifier) to give the title product (32 mg) as a colourless oil. LCMS (2 min, formic) Rt 1.41 min, m/z (ES+) 365 (M+H).

Aufarbeitung

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling
  3. customthe solvent was evaporated in vacuo
  4. customthe crude purified by mass

Quellen und Nachweise

ORD-Eintrag
ord-f81f74f41e2942be813ef9ad80443cdc
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242972B2

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