StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylsilane → Methyl 5-bromo-3-(tetrahydro-2H-thiopyran-4-ylmethyl)-1H-indole-7-carboxylate

HRID 656052
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 656052
[S:1]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH2:3][CH2:2]1.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH3:21][O:22][C:23]([C:25]1[CH:26]=[C:27]([Br:34])[CH:28]=[C:29]2[C:33]=1[NH:32][CH:31]=[CH:30]2)=[O:24].[SiH](CC)(CC)CC>C(Cl)Cl>[Br:34][C:27]1[CH:28]=[C:29]2[C:33](=[C:25]([C:23]([O:22][CH3:21])=[O:24])[CH:26]=1)[NH:32][CH:31]=[C:30]2[CH2:7][CH:4]1[CH2:3][CH2:2][S:1][CH2:6][CH2:5]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 12052TriethylsilaneHCID 65367Trimethylsilyl triflateHCID 20143720Thiane-4-carbaldehydeHCID 24728848methyl 5-bromo-1H-indole-7-carboxylate

Produkt 1

HCID 59332720Methyl 5-bromo-3-(tetrahydro-2H-thiopyran-4-ylmethyl)-1H-indole-7-carboxylateAusbeute 44,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tetrahydro-thiopyran-4-carbaldehyde (1.3 g, 9.84 mmol) in DCM (20 mL) was added TMSOTf (3.5 mL, 19.7 mmol) at 0° C. To this mixture 5-Bromo-1H-indole-7-carboxylic acid methyl ester (2.5 g, 9.84 mmol) was added. After 2 hours, Et3SiH (6.2 mL, 39.4 mmol) was added at 0° C., and stirring continued for 18 hours. The reaction mixture was quenched with sodium bicarbone solution and extracted with DCM. The combined organic layers were dried (MgSO4), concentrated, and purified by column chromatography on silica gel, giving 1.6 g (44%) of the title compound.

Aufarbeitung

  1. waitcontinued for 18 hours
  2. customThe reaction mixture was quenched with sodium bicarbone solution
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-16b2eefdec65464585665ca7220db486
Quelldatensatz
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08071584B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion