Water → 5-(3-chloro-4-cyanophenoxy)-N-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-3-methylpentanamide

HRID 2272593

Reaktionsgleichung

Reaktionsgleichung von HRID 2272593
[CH2:1]([N:3]1[C:15]2[CH:14]=[CH:13][C:12]([NH:16][C:17](=[O:25])[CH2:18][C:19]([OH:24])([CH3:23])[CH2:20][CH2:21][OH:22])=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:2].[Cl:26][C:27]1[CH:34]=[C:33](F)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30].CC(C)([O-])C.[K+].O>C1COCC1>[Cl:26][C:27]1[CH:34]=[C:33]([CH:32]=[CH:31][C:28]=1[C:29]#[N:30])[O:22][CH2:21][CH2:20][C:19]([OH:24])([CH3:23])[CH2:18][C:17]([NH:16][C:12]1[CH:13]=[CH:14][C:15]2[N:3]([CH2:1][CH3:2])[C:4]3[C:9]([C:10]=2[CH:11]=1)=[CH:8][CH:7]=[CH:6][CH:5]=3)=[O:25]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1090002-Chloro-4-fluorobenzonitrileHCID 23665647Potassium tert-butoxideHCID 86729751N-(9-ethyl-9H-carbazol-3-yl)-3,5-dihydroxy-3-methylpentanamide

Produkt 1

HCID 867297525-(3-chloro-4-cyanophenoxy)-N-(9-ethyl-9H-carbazol-3-yl)-3-hydroxy-3-methylpentanamideAusbeute 48,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the compound obtained in Step 1 (348 mg, 1.02 mmol) and 2-chloro-4-fluorobenzonitrile (159 mg, 1.02 mmol) in THF (10 mL) was added potassium t-butoxide (287 mg, 2.56 mmol), and the mixture was stirred at room temperature for 14 hr. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give the title compound (236 mg, 0.496 mmol, 48.5%) as a white powder.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-26ee037a40c04e91beb60a3cfdc1ab90
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120776B2

Verknüpfte Notizen

Wird geladen…