Sodium Bicarbonate → N-(3-furan-2-yl-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide

HRID 25413

Reaction equation

HRID 25413 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N:11]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([CH3:31])(=[O:30])=[O:29])(=[O:21])=[O:20])C(OC(C)(C)C)=O)[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.[O:39]1[CH:43]=[CH:42][CH:41]=[C:40]1B(O)O.C(=O)([O-])O.[Na+]>CN(C)C=O>[O:39]1[CH:43]=[CH:42][CH:41]=[C:40]1[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:28]([CH3:31])(=[O:30])=[O:29])(=[O:20])=[O:21])[CH:9]=2)[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734357Furan-2-boronic acidHCID 22567083tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate

Product 1

HCID 22567203N-(3-furan-2-yl-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamideYield 32.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(3-Furan-2-yl-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide can be obtained as described in Example 47 from 1 g of tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate, 330 mg of 2-furanboronic acid, 40 ml of dimethylformamide, 3.2 ml of a saturated aqueous sodium hydrogencarbonate solution and 42.7 mg of tetrakis(triphenylphosphine)palladium[0]. 200 mg of N-(3-furan-2-yl-1 H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide are thus obtained in the form of a white solid melting at 248° C. (analysis C18H15N3O5S2 % calculated C, 51.79; H, 3.62; N, 10.07; O, 19.16; S, 15.36. % found C, 51.95; H, 3.75; N, 9.68; S, 14.75).

Sources & evidence

ORD record
ord-e2ae363c9d60459b9d55e21340fba99f
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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