Water → HCID 68648162, Verbindung

HRID 1162753

Reaktionsgleichung

Reaktionsgleichung von HRID 1162753
[H-].[Na+].[F:3][C:4]([F:13])([F:12])[C:5]1[C:9]([C:10]#[N:11])=[CH:8][NH:7][N:6]=1.Br[CH2:15][C:16]([NH:18][C:19]1[S:23][C:22]2[CH2:24][CH2:25][CH2:26][CH2:27][C:21]=2[C:20]=1[C:28]([NH2:30])=[O:29])=[O:17].O>CN(C=O)C>[C:10]([C:9]1[C:5]([C:4]([F:3])([F:12])[F:13])=[N:6][N:7]([CH2:15][C:16]([NH:18][C:19]2[S:23][C:22]3[CH2:24][CH2:25][CH2:26][CH2:27][C:21]=3[C:20]=2[C:28]([NH2:30])=[O:29])=[O:17])[CH:8]=1)#[N:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 595205232-(2-Bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideHCID 178510441HCID 178510441, Verbindung

Produkt 1

HCID 68648162HCID 68648162, VerbindungAusbeute 49 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (60% [w/w] suspension in oil, 130 mg, 3.25 mmol) was added to a solution of 3-(trifluoromethyl)-4-cyanopyrazole (520 mg, 3.23 mmol) in DMF (10 mL). The reaction mixture was stirred at RT for 1 h before adding 2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (1.023 g, 3.23 mmol). The reaction mixture was heated at 65° C. for 4 h then allowed to cool to RT. Water (20 mL) was added and the reaction mixture extracted with EtOAc (3×20 mL). The combined EtOAc layers were washed with water (5×20 mL), brine (20 mL), dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the crude reaction mixture as a cream solid. Purification by flash chromatography (eluent 1:1 EtOAc:heptane) gave desired product (626 mg, 1.58 mmol, 49%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated at 65° C. for 4 h
  2. temperatureto cool to RT
  3. extractionthe reaction mixture extracted with EtOAc (3×20 mL)
  4. washThe combined EtOAc layers were washed with water (5×20 mL), brine (20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customto give the crude
  9. customreaction mixture as a cream solid
  10. customPurification by flash chromatography (eluent 1:1 EtOAc:heptane)

Quellen und Nachweise

ORD-Eintrag
ord-e871e359d413404cbd5beed4d5fe133a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820707B2

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