Sodium hydride → 6-Bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonate

HRID 1094658

Reaktionsgleichung

Reaktionsgleichung von HRID 1094658
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]([OH:18])([CH3:17])[C:13]([F:16])([F:15])[F:14])[CH:6]=[CH:5]2.[H-].[Na+].[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[CH3:21][S:22]([O:18][C:12]([C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=2)[N:8]=1)([CH3:17])[C:13]([F:15])([F:14])[F:16])(=[O:24])=[O:23]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 574581662-(6-Bromoquinolin-2-yl)-1,1,1-trifluoropropan-2-ol

Produkt 1

HCID 574581676-Bromoquinolin-2-yl-2,2,2-trifluoro-1-methylethyl methanesulfonateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a solution of 6-Bromo-quinolin-2-yl-1,1,1-trifluoropropan-2-ol (5.06 g, 15.8 mmol) in THF (50 ml) was added sodium hydride (1.26 g, 31.6 mmol) portionwise at 0° C. and the mixture was stirred at room temperature for 2 hour. A solution of methanesulfonyl chloride (3.62 g, 31.6 mmol) in THF (10 ml) was added there at 0°. Then the reaction mixture was stirred at room temperature for 2 hours. The mixture was quenched with saturated sodium bicarbonate aqueous solution, and the product was extracted with ethyl acetate which was dried over sodium sulfate. Then, filtration, evaporation, purification through silica gel column chromatography eluting with hexane/ethyl acetate (15:1 to 5:1) furnished the title compound (6.29 g, 84% yield) as a white solid. 1H NMR (300 MHz, CDCl3) ppm 2.45 (3H, s), 3.24 (3H, s), 7.81-7.86 (2H, m), 7.96-8.05 (2H, m), 8.17 (1H, d, J=8.8 Hz). MS (ESI): m/z 397, 399 (M+H)+.

Aufarbeitung

  1. stirringThen the reaction mixture was stirred at room temperature for 2 hours
  2. customThe mixture was quenched with saturated sodium bicarbonate aqueous solution
  3. extractionthe product was extracted with ethyl acetate which
  4. dry with materialwas dried over sodium sulfate
  5. filtrationThen, filtration, evaporation, purification through silica gel column chromatography
  6. washeluting with hexane/ethyl acetate (15:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-3079872587b24efdb9c524c09119438a
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08134004B2

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