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

HRID 25437

Reaktionsgleichung

Reaktionsgleichung von HRID 25437
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1B(O)O)=O)(C)(C)C.C(=O)([O-])O.[Na+].I[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([N:35]([S:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)(=[O:45])=[O:44])C(OC(C)(C)C)=O)[CH:33]=2)[N:28](C(OC(C)(C)C)=O)[N:27]=1>CN(C)C=O>[NH:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[C:32]([NH:35][S:43]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)(=[O:44])=[O:45])[CH:33]=2)[NH:28][N:27]=1

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 68877978tert-butyl 3-iodo-5-(N-tert-butoxycarbonylbenzenesulfonylamino)indazole-1-carboxylate

Produkt 1

HCID 135621938N-[3-(1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamideAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
122 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. temperatureAfter cooling to a temperature in the region of 20° C.
  2. filtrationthe catalyst is filtered through a bed of Celite® 535
  3. concentrationthe filtrate is concentrated to dryness under reduced pressure
  4. customThe reaction crude
  5. customis purified by preparative HPLS chromatography
  6. additionThe fractions containing the expected product
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-f6f7ddfec69b42338710682d21381dc1
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06858638B2

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