Reaktion #53715

Reaktionsgleichung

N-tert-butoxycarbonylindole-2-boronic acid

sodium hydrogencarbonate

tert-butyl 3-iodo-5-(N-tert-butoxycarbonylbenzenesulfonylamino)indazole-1-carboxylate

→

N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide

Ausbeute 66.3%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to a temperature in the region of 20° C.
2. 2
   Filtrationthe catalyst is filtered through a bed of Celite® 535
3. 3
   Einengenthe filtrate is concentrated to dryness under reduced pressure
4. 4
   SonstigeThe reaction crude
5. 5
   Sonstigeis purified by preparative HPLS chromatography
6. 6
   workup.ADDITIONThe fractions containing the expected product
7. 7
   Einengenconcentrated

Vorschrift

N-[3-(1H-Indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide can be obtained in the following way: 158.1 mg of N-tert-butoxycarbonylindole-2-boronic acid and 360 μl of a saturated sodium hydrogencarbonate solution and then 48.2 mg of tetrakis(triphenyl-phosphine)palladium[0] are added to a solution of 101.9 mg of tert-butyl 3-iodo-5-(N-tert-butoxycarbonylbenzenesulfonylamino)indazole-1-carboxylate in 4.5 ml of dimethylformamide. The suspension is heated in the region of 122° C. for 16 hours. After cooling to a temperature in the region of 20° C., the catalyst is filtered through a bed of Celite® 535, and the filtrate is concentrated to dryness under reduced pressure. The reaction crude is purified by preparative HPLS chromatography coupled to a mass detector (LC/MS, conditions A). The fractions containing the expected product are pooled and concentrated. 43.8 mg of N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide are obtained in the form of the trifluoroacetate salt (LC/MS analysis: Tr=3.49 minutes; [M+H]+=389.13).

Quelle