1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazole

HRID 41120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 41120
[C:1]1([C:7]2[CH:8]=[C:9]([C:16]([OH:18])=O)[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC[N:21]=[C:22]=[N:23]CCCN(C)C.[CH:30]1[CH:31]=[CH:32][C:33]2N(O)N=[N:36][C:34]=2[CH:35]=1.O1CCO[CH2:42][CH2:41]1>>[NH:36]1[C:34]2[C:33](=[CH:32][C:31]([C:22]3[N:23]=[C:16]([C:9]4[S:10][C:11]([C:12]([F:13])([F:14])[F:15])=[C:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)[CH:8]=4)[O:18][N:21]=3)=[CH:30][CH:35]=2)[CH:42]=[CH:41]1

Komponenten

5

Edukt 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 312751,4-DioxaneHCID 757711-HydroxybenzotriazoleHCID 27833724-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid

Produkt 1

HCID 251103463-(1H-indol-5-yl)-5-(4-phenyl-5-(trifluoromethyl)thiophen-2-yl)-1,2,4-oxadiazoleAusbeute 46,7 %

Versuchsvorschrift

To a solution of 4-phenyl-5-(trifluoromethyl)-2-thiophenecarboxylic acid in 1,4-dioxane were added under nitrogen atmosphere EDCI (125 mg, 0.65 mmol) and HOBt (88 mg, 0.65 mmol). The reaction was stirred at room temperature for 30 min followed by addition of N-hydroxyimidamide (114 mg, 0.65 mmol), the reaction was stirred for 30 additional minutes at room temperature followed by 16 h at 95° C. The reaction was concentrated under reduced pressure. The crude was diluted with EtOAc (80 mL) and washed with a saturated solution of NaHCO3 (2×50 ml). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (9:1) to yield 91 mg (46.7%) of the product. MS (EI) m/z: 412 (M+).

Aufarbeitung

  1. stirringthe reaction was stirred for 30 additional minutes at room temperature
  2. waitfollowed by 16 h at 95° C
  3. concentrationThe reaction was concentrated under reduced pressure
  4. additionThe crude was diluted with EtOAc (80 mL)
  5. washwashed with a saturated solution of NaHCO3 (2×50 ml)
  6. dry with materialThe organic phase was dried over Na2SO4 anhydrous
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-61edddd510d947c3bccf1be37092a182
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08530503B2

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