Hydrochloric Acid → 2h-Pyrrolo[2,3-b]pyridin-2-one,3-fluoro-1,3-dihydro-3-methyl-1-phenyl-

HRID 1646955

Reaktionsgleichung

Reaktionsgleichung von HRID 1646955
[CH3:1][CH:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]1=[O:17].[H-].[Na+].[F:20]N(CC(C)(C)C)S(C1C=CC(C)=CC=1)(=O)=O.Cl>C1COCC1.ClCCl>[F:20][C:2]1([CH3:1])[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[N:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:3]1=[O:17]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 145159p-Tolyl-N-fluoro-N-neopentylsulfonamideHCID 147395072h-Pyrrolo[2,3-b]pyridin-2-one,1,3-dihydro-3-methyl-1-phenyl-

Produkt 1

HCID 147395242h-Pyrrolo[2,3-b]pyridin-2-one,3-fluoro-1,3-dihydro-3-methyl-1-phenyl-

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Add 1,3-dihydro-3-methyl-1-phenyl-2H-pyrrolo[2,3-b]-pyridin-2-one (H) (3.0 g, 0.013 mole) portionwise to sodium hydride (0.63 g of 60% NaH in oil, 0.015 mole, washed with hexane) in dry THF (35 mL) at 10° C. under a N2 atmosphere. Stir for 30 minutes at room temperature, and then recool to 10° C. Add N-fluoro-N-neopentyl-p-toluenesulfonamide (4.1 g, 0.015 mole) in dry THF (30 mL) dropwise over 10 minutes. Warm reaction mixture up to room temperature slowly, and stir for 16 hours. Pour onto ice/water (100 mL), and neutralize to pH=4 to 5 with 15% aqueous HCl. Separate layers. Dry organic solution with MgSO4, filter, and rotoevaporate to give an oil. Dissolve the oil in dichloromethane, and chromatograph on silica gel, eluting with 30% ethyl acetate-hexane. Combine the appropriate fractions, and concentrate under reduced pressure. Triturate with isopropyl ether-petroleum ether and filter to give the title compound AA as a white solid (1.1 g, m.p. 83°-85° C.).

Aufarbeitung

  1. customrecool to 10° C
  2. temperatureWarm
  3. customreaction mixture up to room temperature slowly
  4. stirringstir for 16 hours
  5. additionPour onto ice/water (100 mL)
  6. filtrationDry organic solution with MgSO4, filter
  7. customrotoevaporate to give an oil
  8. washchromatograph on silica gel, eluting with 30% ethyl acetate-hexane
  9. concentrationconcentrate under reduced pressure
  10. customTriturate with isopropyl ether-petroleum ether
  11. filtrationfilter

Quellen und Nachweise

ORD-Eintrag
ord-746d2d03e09c433abdf12fff7d23d02d
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05182289

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