Methanesulfonic Acid → N-tetrahydropyranyl-2-hydroxycarbazole

HRID 2410267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2410267
CC1C=C(C)N(C2C=C(C=CC=2)OC2C=CC3C4C(=CC=CC=4)NC=3C=2)N=1.CC1C=C(C)N(C2C=C(C=CC=2)[O:38][C:39]2[CH:51]=[CH:50][C:49]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[N:42]([CH:52]4[CH2:57][CH2:56][CH2:55][CH2:54][O:53]4)[C:41]=3[CH:40]=2)N=1.S(O)(C)(=O)=O.C(=O)(O)[O-].[Na+]>CO.CCCCCC.C(OCC)(=O)C>[O:53]1[CH2:54][CH2:55][CH2:56][CH2:57][CH:52]1[N:42]1[C:41]2[CH:40]=[C:39]([OH:38])[CH:51]=[CH:50][C:49]=2[C:48]2[C:43]1=[CH:44][CH:45]=[CH:46][CH:47]=2

Komponenten

7

Edukt 4

HCID 6395Methanesulfonic AcidHCID 516892Sodium BicarbonateHCID 681812542-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-carbazoleHCID 681813132-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-N-(tetrahydropyranyl)carbazole

Produkt 1

HCID 68181306N-tetrahydropyranyl-2-hydroxycarbazoleAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

In another step, 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-carbazole was synthesized. To a 50 mL round flask was added with the solution of 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-N-(tetrahydropyranyl)carbazole (0.49 g, 1.12 mmol) and MsOH (0.36 mL, 5.6 mmol) in methanol (20 mL), and the mixture was kept at rt for 30 minutes then 50° C. for 1.5 hours. TLC showed that all the protected starting material was transferred, and then trace sodium bicarbonate was added into the system to quench the reaction. The resulting product was directly treated with an flash column using hexane/ethyl acetate=3:1 as eluent to give N-tetrahydropyranyl-2-hydroxycarbazole as a white solid. (0.32 g, 81% yield).

Aufarbeitung

  1. wait50° C. for 1.5 hours
  2. additionwas added into the system
  3. customto quench
  4. customthe reaction
  5. additionThe resulting product was directly treated with an flash column

Quellen und Nachweise

ORD-Eintrag
ord-7b3eb91705b94dd2a3458beca6396da6
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816080B2

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