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N,N'-Dimethylethylenediamine → 2,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-dimethylsulfamoyl-3-methyl-phenyl)-amide

HRID 383741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 383741
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:13])[CH3:12])(=[O:10])=[O:9])=[C:4]([CH3:14])[CH:3]=1.[CH3:15][C:16]1[N:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:31]([F:34])([F:33])[F:32])[C:18]([CH3:24])=[CH:19][C:20]=1[C:21]([NH2:23])=[O:22].C([O-])([O-])=O.[K+].[K+].CNCCNC>CCOC(C)=O.[Cu]I.C1(C)C=CC=CC=1>[CH3:12][N:11]([CH3:13])[S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:23][C:21]([C:20]2[CH:19]=[C:18]([CH3:24])[N:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([F:33])([F:32])[F:34])[C:16]=2[CH3:15])=[O:22])=[CH:3][C:4]=1[CH3:14])(=[O:10])=[O:9]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 595902374-bromo-N,N,2-trimethylbenzenesulfonamideHCID 598082232,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxamide

Produkt 1

HCID 598078142,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxylic acid (4-dimethylsulfamoyl-3-methyl-phenyl)-amide
Ausbeute 79.246,703 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

An oven-dried, argon-sparged vial was charged with 4-bromo-2,N,N-trimethyl-benzenesulfonamide (70 mg, 0.25 mmol), 2,5-dimethyl-1-(2-trifluoromethyl-phenyl)-1H-pyrrole-3-carboxamide (85 mg, 0.30 mmol), anhyd K2CO3 (69 mg, 0.50 mmol), and copper (I) iodide (10 mg, 0.05 mmol), and then briefly sparged with argon. To the vial under argon was added anhyd toluene (0.5 mL) and N,N′-dimethyl-ethylenediamine (11 μL, 0.10 mmol), then capped and heated at 120° C. After 24 h the reaction mixture was cooled, diluted with EtOAc, filtered through Celite and concentrated under reduced pressure. The crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 50:50) to afford the title compound (95 g, 79%) as a white solid. 1H-NMR (DMSO-d6) δ 9.74 (1H, s), 8.01 (1H, d, J=7.8), 7.92 (1H, app t, J=7.8), 7.78-7.86 (3H, m), 7.71 (1H, d, J=8.3), 7.51 (1H, d, J=7.8), 6.65 (1H, s), 2.69 (6H, s), 2.53 (3H, s), 2.14 (3H, s), 1.88 (3H, s); MS(ESI): 480 (MH+).

Aufarbeitung

  1. customAn oven-dried, argon-sparged vial
  2. custombriefly sparged with argon
  3. customcapped
  4. temperatureAfter 24 h the reaction mixture was cooled
  5. filtrationfiltered through Celite
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was chromatographed (silica, EtOAc/Hex, 0:100 to 50:50)

Quellen und Nachweise

ORD-Eintrag
ord-e91362245d3c4d288396aebb904ba55c
Quelldatensatz
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08367667B2

Notizen zur Reaktion

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