Reaktion #53687

ord-957820a86bfd4fb99ef3efcd47696aea

Reaktionsgleichung

O=[N+]([O-])c1ccccc1B(O)O
2-nitrophenylboronic acid
CC(C)(C)OC(=O)N(c1ccc2c(c1)c(I)nn2C(=O)OC(C)(C)C)S(=O)(=O)c1ccccc1S(C)(=O)=O
tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate
CN(C)C=O
dimethylformamide
O=C([O-])O.[Na+]
sodium hydrogencarbonate
→
CS(=O)(=O)c1ccccc1S(=O)(=O)Nc1ccc2[nH]nc(-c3ccccc3[N+](=O)[O-])c2c1
N-[3-(2-nitrophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide
Ausbeute 16.2%

Edukte

—
tetrakis(triphenylphosphine)palladium[0]
O=[N+]([O-])c1ccccc1B(O)O
2-nitrophenylboronic acid
CC(C)(C)OC(=O)N(c1ccc2c(c1)c(I)nn2C(=O)OC(C)(C)C)S(=O)(=O)c1ccccc1S(C)(=O)=O
tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate
CN(C)C=O
dimethylformamide
O=C([O-])O.[Na+]
sodium hydrogencarbonate

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O.ClCCl
dichloromethane ethyl acetate

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

N-[3-(2-Nitrophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide can be obtained as described in Example 47 from 620 mg of tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate, 202 mg 2-nitrophenylboronic acid, 2 ml of a saturated aqueous sodium hydrogencarbonate solution, 31.7 mg of tetrakis(triphenylphosphine)palladium[0] and of 20 ml of dimethylformamide. 70 mg of N-[3-(2-nitrophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide are thus obtained in the form of a yellow solid (Rf=0.53 silica gel thin layer chromatography, eluent: dichloromethane/ethyl acetate (80-20 by volume)).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858638B2uspto-grants-2005_02