Hydrochloric Acid → (E)-2-(4-((E)-1-(1H-Indazol-5-yl)-2-phenylbut-1-en-1-yl)phenyl)ethenesulfonamide

HRID 1057212Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057212
Br[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:19]=[C:20]3[C:24](=[CH:25][CH:26]=2)[N:23](C2CCCCO2)[N:22]=[CH:21]3)=[C:9](\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH2:10][CH3:11])=[CH:4][CH:3]=1.[CH:33]([S:35]([NH2:38])(=[O:37])=[O:36])=[CH2:34].C(N(CC)CC)C.Cl>CN(C=O)C.CCO.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH:23]1[C:24]2[C:20](=[CH:19][C:18](/[C:8](/[C:5]3[CH:6]=[CH:7][C:2](/[CH:34]=[CH:33]/[S:35]([NH2:38])(=[O:37])=[O:36])=[CH:3][CH:4]=3)=[C:9](/[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)\[CH2:10][CH3:11])=[CH:26][CH:25]=2)[CH:21]=[N:22]1

Komponenten

9

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 520075Vinyl sulfonamideHCID 66802799(E)-5-(1-(4-Bromophenyl)-2-phenylbut-1-en-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Produkt 1

HCID 66802069(E)-2-(4-((E)-1-(1H-Indazol-5-yl)-2-phenylbut-1-en-1-yl)phenyl)ethenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of (E)-5-(1-(4-bromophenyl)-2-phenylbut-1-en-1-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (0.1 g, 0.25 mmol), ethenesulfonamide (80 mg, 0.74 mmol), Pd(Ph3P)2Cl2 (18 mg, 0.025 mmol), triethylamine (0.25 g, 2.5 mmol) in DMF (1.25 mL) was degassed with 3 vacuum/nitrogen cycles, heated at 100° C. overnight, and then cooled to room temperature. The reaction mixture was diluted with water, extracted with EtOAc, washed with water, brine, dried over sodium sulfate, and filtered. The filtrate was concentrated down to give a residue that was redissolved in EtOH (2.5 ml). HCl (0.5 mL, 1.25 N HCl in ethanol) was added, and the mixture was heated at 80° C. for 1 h, diluted with water, and then extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with water, brine, dried over sodium sulfate, filtered, and concentrated to give the crude product. This crude material was purified on a RP-C18 column using 30-100% acetonitrile in water in the presence of 0.1% TFA to afford the title compound. LCMS: 430 (M+H)+.

Aufarbeitung

  1. customwas degassed with 3 vacuum/nitrogen cycles
  2. temperaturecooled to room temperature
  3. additionThe reaction mixture was diluted with water
  4. extractionextracted with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated down
  9. customto give a residue that
  10. temperaturethe mixture was heated at 80° C. for 1 h
  11. extractionextracted with ethyl acetate (2×50 mL)
  12. washThe combined organic layers were washed with water, brine
  13. dry with materialdried over sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated
  16. customto give the crude product
  17. customThis crude material was purified on a RP-C18 column

Quellen und Nachweise

ORD-Eintrag
ord-f1535e8e78424b5b8c384853afa896ac
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09399646B2

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