Pyridine → 5-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide

HRID 623363Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 623363
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([S:8](Cl)(=[O:10])=[O:9])=[N:6][CH:7]=1.N1C=CC=CC=1.[F:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][CH2:26][CH:27]([CH3:29])[CH3:28])=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl.O>[F:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]([CH2:26][CH:27]([CH3:29])[CH3:28])[S:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)(=[O:10])=[O:9])=[CH:21][CH:20]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 516892Sodium BicarbonateHCID 185437114-Fluoro-N-(2-methylpropyl)anilineHCID 445580975-Bromopyridine-2-sulfonyl chloride

Produkt 1

HCID 867218735-Bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amideAusbeute 82,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-bromo-pyridine-2-sulfonyl chloride (330 mg, 1.29 mmol) in DCM (10 mL) was added pyridine (208 μL, 2.57 mmol) followed by a solution of (4-fluoro-phenyl)-isobutyl-amine (215 mg, 1.29 mmol) in DCM (10 mL) and the reaction was stirred at room temperature for 16 hours. Water and saturated aqueous NaHCO3 were added and then extracted with DCM, filtered through a phase separator, concentrated then purified by silica gel column chromatography (0-20% EtOAc in cyclohexane) to give 5-bromo-pyridine-2-sulfonic acid (4-fluoro-phenyl)-isobutyl-amide (414 mg, 78%). LCMS (m/z, Method A) ES+ 387/389 [M+1]+.

Aufarbeitung

  1. extractionextracted with DCM
  2. filtrationfiltered through a phase separator
  3. concentrationconcentrated
  4. customthen purified by silica gel column chromatography (0-20% EtOAc in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-7db6ec00e5934fa78fb19a674a039574
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09302985B2

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