Réaction #76802

Équation de réaction

Sodium hydride

4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

thiophenol

methanol

→

title compound

Rendement 52.0%

4′-Phenylthiospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine]

Rendement 52.0%

Solvants

water

dioxane

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was refluxed for 4 days
2. 2
   Extractionextracted with chloroform (3×30 mL)
3. 3
   ExtractionThe combined organic extract
4. 4
   Séchagewas dried over anhydrous magnesium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   Autrethe residue flash chromatographed on neutral silica gel using
7. 7
   workup.ADDITIONa 98:2 mixture of ammoniated chloroform/methanol

Mode opératoire

Sodium hydride (151 mg, 3.77 mmol) was added to a solution of 97 mg (0.387 mmol) of 4′-chlorospiro[1-azabicyclo[2.2.2]octane-3,2′(3′H)-furo[2,3-b]pyridine], 0.40 mL (3.91 mmol) of thiophenol and 0.10 mL of methanol in 15 mL of dioxane, under a nitrogen atmosphere. The reaction was refluxed for 4 days, cooled to ambient temperature, diluted with 30 mL of water, and extracted with chloroform (3×30 mL). The combined organic extract was dried over anhydrous magnesium sulfate, concentrated in vacuo and the residue flash chromatographed on neutral silica gel using a 98:2 mixture of ammoniated chloroform/methanol to give 65 mg (52%) of the title compound as a colourless oil: electrospray MS (m/z, relative intensity) 325 ([MH]+).

Source