2,6-Lutidine → HCID 58677022, Verbindung

HRID 1518237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1518237
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][OH:27])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:42]([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43])(=O)=O>CCOC(C)=O>[Si:42]([O:27][CH2:26][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:8]1[NH:9][C:10]2[C:15]([C:7]=1[CH:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)=[CH:14][CH:13]=[C:12]([C:16]([O:18][CH3:19])=[O:17])[CH:11]=2)([C:45]([CH3:48])([CH3:47])[CH3:46])([CH3:44])[CH3:43]

Komponenten

5

Edukt 3

HCID 79372,6-LutidineHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonateHCID 58677008methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate

Produkt 1

HCID 58677022HCID 58677022, VerbindungAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution (0.039 M) of methyl 3-cyclohexyl-2-[2-(hydroxymethyl)phenyl]-1H-indole-6-carboxylate was treated with 2,6-lutidine (2 eq) and then with tert-butyl(dimethyl)silyl trifluoromethanesulfonate (1.2 eq). The solution was stirred for 15 min. Removal of the volatiles in vacuo gave a residue that was diluted with EtOAc, washed with 1N HCl, saturated aqueous NaHCO3, brine, dried and concentrated in vacuo to afford the title compound (90%) as a solid. MS (ES+) m/z 478 (M+H+).

Aufarbeitung

  1. customRemoval of the volatiles in vacuo
  2. customgave a residue that
  3. washwashed with 1N HCl, saturated aqueous NaHCO3, brine
  4. customdried
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-57ee829d780d4a8fa10879b61cf14316
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232390B2

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