تفاعل #53694

ord-3e2a4ae2108843d5942a4a178989a99b

معادلة التفاعل

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
COc1ccc2c(c1)cc(B(O)O)n2C(=O)OC(C)(C)C
1-(tert-butoxycarbonyl)-5-methoxy-indole-2-boronic acid
O=C([O-])O.[Na+]
sodium hydrogencarbonate
→
COc1ccc2[nH]c(-c3n[nH]c4ccc(NS(=O)(=O)c5ccccc5S(C)(=O)=O)cc34)cc2c1
2-methylsulfonyl-N-[3-(5-methoxy-1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide
المردود 19.3%

المتفاعلات

—
tetrakis(triphenylphosphine)palladium[0]
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
COc1ccc2c(c1)cc(B(O)O)n2C(=O)OC(C)(C)C
1-(tert-butoxycarbonyl)-5-methoxy-indole-2-boronic acid
O=C([O-])O.[Na+]
sodium hydrogencarbonate

الكواشف

لا شيء

المذيبات

CN(C)C=O
dimethyl-formamide

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

2-Methylsulfonyl-N-[3-(5-methoxy-1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide can be obtained as described in Example 47 from 1.77 g of tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)-indazole-1-carboxylate, 1.52 g 1-(tert-butoxycarbonyl)-5-methoxy-indole-2-boronic acid, 70 ml of dimethyl-formamide, 5.65 ml of a saturated aqueous sodium hydrogencarbonate solution and 151 mg of tetrakis(triphenylphosphine)palladium[0]. 250 mg of 2-methylsulfonyl-N-[3-(5-methoxy-1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide are thus obtained in the form of an amorphous cream solid (LC/MS analysis: Tr 3.52 minutes MH+=497).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06858638B2uspto-grants-2005_02