Dimethylformamide → 7-[(3-Fluorophenyl)sulfanyl]-3,4,5',6'-tetrahydro-2H,4'H-spiro[1-benzofuro[2,3-c]pyridine-1,3'-pyran]

HRID 1616868Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1616868
I[C:2]1[CH:7]=[CH:6][C:5]2[C:8]3[CH2:19][CH2:18][NH:17][C:11]4([CH2:16][CH2:15][CH2:14][O:13][CH2:12]4)[C:9]=3[O:10][C:4]=2[CH:3]=1.CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.CN(C=O)C.[F:41][C:42]1[CH:43]=[C:44]([SH:48])[CH:45]=[CH:46][CH:47]=1.CC(C)([O-])C.[Na+]>N#N.[Cu]I>[F:41][C:42]1[CH:43]=[C:44]([S:48][C:2]2[CH:7]=[CH:6][C:5]3[C:8]4[CH2:19][CH2:18][NH:17][C:11]5([CH2:16][CH2:15][CH2:14][O:13][CH2:12]5)[C:9]=4[O:10][C:4]=3[CH:3]=2)[CH:45]=[CH:46][CH:47]=1

Komponenten

8

Edukt 5

HCID 6228DimethylformamideHCID 652372,9-Dimethyl-1,10-phenanthrolineHCID 75710m-FluorobenzenethiolHCID 23676156Sodium t-butoxideHCID 673239207-Iodo-3,4,5',6'-tetrahydro-2H,4'H-spiro[1-benzofuro[2,3-c]pyridine-1,3'-pyran]

Produkt 1

HCID 673228897-[(3-Fluorophenyl)sulfanyl]-3,4,5',6'-tetrahydro-2H,4'H-spiro[1-benzofuro[2,3-c]pyridine-1,3'-pyran]

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 947NitrogenLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

7-Iodo-3,4,5′,6′-tetrahydro-2H,4′H-spiro[1-benzofuro[2,3-c]pyridine-1,3′-pyran] (0.20 g, 0.56 mmol), neocuproine (11.6 mg, 0.0558 mmol) and copper(I) iodide (53.1 mg, 0.279 mmol) were dissolved into the anhydrous DMF (4 mL, 50 mmol) in a 20 mL scintillation vial under N2. 3-Fluoro-benzenethiol (104 μL, 1.23 mmol) was added neat followed immediately by the addition of the sodium tert-butoxide (118 mg, 1.23 mmol). The reaction vial was capped with a teflon coated cap and the mixture was stirred at 100° C. overnight. After 15 h, the reaction was cooled to room temperature and concentrated under vacuum. The residual solid was partially dissolved into a 5% MeOH in DCM solution and flushed through a Celite plug. The concentrated filtrate was chromatographed on silica gel using DCM-MeOH—NH4OH to afford a brownish oil, used directly in the next step.

Aufarbeitung

  1. customcap
  2. waitAfter 15 h
  3. temperaturethe reaction was cooled to room temperature
  4. concentrationconcentrated under vacuum
  5. dissolutionThe residual solid was partially dissolved into a 5% MeOH in DCM solution
  6. customflushed through a Celite plug
  7. customThe concentrated filtrate was chromatographed on silica gel
  8. customto afford a brownish oil

Quellen und Nachweise

ORD-Eintrag
ord-6602114c734f440793814d7085c009ed
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08765779B2

Notizen zur Reaktion

Wird geladen…