Reaktion #646363

Reaktionsgleichung

H2O

{4-[3-(4-bromophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]thiazol-2-ylmethyl}carbamic acid benzyl ester

thioanisole

→

6-(2-Aminomethylthiazol-4-yl)-3-(4-bromophenyl)-1,9-dimethyl-1,9-dihydro-pyrido[2,3-b]indol-2-one

Lösungsmittel

TFA

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe mixture is extracted with EtOAc
2. 2
   Waschenthe organic phases are washed with H2O
3. 3
   Trocknenthe product is dried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   SonstigePurification
7. 7
   Waschenis carried out by chromatography on a silica column, elution
8. 8
   Filtrationthe product is filtered
9. 9
   Waschenwashed with a minimum amount of Et2O

Vorschrift

A solution of compound A {4-[3-(4-bromophenyl)-1,9-dimethyl-2-oxo-2,9-dihydro-1H-pyrido[2,3-b]indol-6-yl]thiazol-2-ylmethyl}carbamic acid benzyl ester (200 mg, 0.32 mmol) and thioanisole (308 μl, 2.60 mmol) in 2 ml of TFA is left to stir overnight at ambient temperature. H2O is added, the mixture is extracted with EtOAc, the organic phases are washed with H2O and the product is dried over MgSO4, filtered and concentrated. Purification is carried out by chromatography on a silica column, elution being carried out with 100% EtOAc and then with an EtOAc/5% MeOH mixture then with an EtOAc/5% MeOH/1% TEA mixture. The residue is taken up in a 1/1 EtOAc/Et2O mixture and the product is filtered and washed with a minimum amount of Et2O.

Quelle