Water → 2-(2-(4-Formyl-3-(trifluoromethyl)pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide

HRID 1162756

Reaktionsgleichung

Reaktionsgleichung von HRID 1162756
[F:1][C:2]([F:11])([F:10])[C:3]1[C:7]([CH:8]=[O:9])=[CH:6][NH:5][N:4]=1.[H-].[Na+].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>[CH:8]([C:7]1[C:3]([C:2]([F:1])([F:10])[F:11])=[N:4][N:5]([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:6]=1)=[O:9]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 595205232-(2-Bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideHCID 178519884HCID 178519884, Verbindung

Produkt 1

HCID 595204952-(2-(4-Formyl-3-(trifluoromethyl)pyrazol-1-yl)acetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

3-(trifluoromethyl)pyrazole-4-carbaldehyde (200 mg, 1.22 mmol) was dissolved in DMF (10 mL). NaH (60% [w/w] suspension in oil, 50 mg, 1.25 mmol) was added portionwise and the reaction mixture stirred at RT for 30 min. 2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide (386 mg, 1.22 mmol) was added and the reaction mixture heated at 65° C. for 2 h, then allowed to cool to RT. Water (10 mL) was added and the reaction mixture extracted with EtOAc (3×10 mL). The combined EtOAc layers were washed with water (5×10 mL), brine (10 mL), dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the desired product (470 mg, 1.17 mmol, 96%).

Aufarbeitung

  1. temperaturethe reaction mixture heated at 65° C. for 2 h
  2. temperatureto cool to RT
  3. extractionthe reaction mixture extracted with EtOAc (3×10 mL)
  4. washThe combined EtOAc layers were washed with water (5×10 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-19cb5c3c30c441699cdbcdaecd71a502
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820707B2

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