Reaktion #646442

Reaktionsgleichung

DAST

3-(2,4-dichlorophenyl)-6-(2-hydroxymethylthiazol-4-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

H2O

(diethylamino)sulphur trifluoride

→

3-(2,4-Dichlorophenyl)-6-(2-fluoromethylthiazol-4-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITthe mixture is left
2. 2
   workup.STIRRINGto stir at ambient temperature for a further 16 hours
3. 3
   Extraktionthe mixture is extracted with CH2Cl2
4. 4
   Trocknenthe organic phase is dried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated to dryness
7. 7
   SonstigePurification
8. 8
   Waschenis carried out on a silica column, elution
9. 9
   Filtrationthe precipitate is filtered off
10. 10
    Waschenwashed with MeOH

Vorschrift

150 mg (0.319 mmol) of compound from Example 9, 3-(2,4-dichlorophenyl)-6-(2-hydroxymethylthiazol-4-yl)-1,9-dimethyl-1,9-dihydropyrido[2,3-b]indol-2-one, are dissolved in 3 ml of CH2Cl2. 51 μl of (diethylamino)sulphur trifluoride (DAST) are added at 0° C. The mixture is stirred at 0° C. for 2 hours. A further 100 μl of DAST are added (presence of starting product) and the mixture is left to stir at ambient temperature for a further 16 hours. H2O is added, the mixture is extracted with CH2Cl2, and the organic phase is dried over MgSO4, filtered and concentrated to dryness, adsorbing onto silica. Purification is carried out on a silica column, elution being carried out with EtOAc/40% cyclohexane and then with EtOAc/30% cyclohexane. The residue is taken up in MeOH and the precipitate is filtered off, and washed with MeOH and then with a minimum amount of Et2O.

Quelle