Reaktion #53695

ord-5b32db8810814a1cbd9434d89ecd6041

Reaktionsgleichung

CC(C)(C)OC(=O)n1nc(I)c2cc(NS(=O)(=O)c3ccccc3S(C)(=O)=O)ccc21
tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate
CC(C)(C)OC(=O)n1cccc1B(O)O
1-(tert-butyloxycarbonyl)pyrrole-2-boronic acid
O=C([O-])O.[Na+]
sodium hydrogencarbonate
→
CS(=O)(=O)c1ccccc1S(=O)(=O)Nc1ccc2[nH]nc(-c3ccc[nH]3)c2c1
2-methylsulfonyl-N-[3-(1H-pyrrol-2-yl)-1H-indazol-5-yl]benzenesulfonamide
Ausbeute 29.9%

Edukte

—
tetrakis(triphenylphosphine)palladium[0]
CC(C)(C)OC(=O)n1nc(I)c2cc(NS(=O)(=O)c3ccccc3S(C)(=O)=O)ccc21
tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate
CC(C)(C)OC(=O)n1cccc1B(O)O
1-(tert-butyloxycarbonyl)pyrrole-2-boronic acid
—
solid
O=C([O-])O.[Na+]
sodium hydrogencarbonate

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

2-Methylsulfonyl-N-[3-(1H-pyrrol-2-yl)-1H-indazol-5-yl]benzenesulfonamide can be obtained as described in Example 59 from 0.5 g of tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate, 365 mg of 1-(tert-butyloxycarbonyl)pyrrole-2-boronic acid, 20 ml of dimethylformamide, 1.87 ml of saturated aqueous sodium hydrogencarbonate solution and 24.5 mg of tetrakis(triphenylphosphine)palladium[0]. 108 mg of 2-methylsulfonyl-N-[3-(1H-pyrrol-2-yl)-1H-indazol-5-yl]benzenesulfonamide are thus obtained in the form of a pale green solid melting at 255° C. (analysis C18H16N4O4S2 % calculated: C, 51.91; H, 3.87; N, 13.45; O, 15.37; S, 15.40. % found C, 51.63; H, 3.87; N, 13.27; S, 15.21).

Quelle

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