Sodium Bicarbonate → 2-methylsulfonyl-N-(3-pyridin-4-yl-1H-indazol-5-yl)benzenesulfonamide

HRID 25414

Reaction equation

HRID 25414 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.[N:39]1[CH:44]=[CH:43][C:42](B(O)O)=[CH:41][CH:40]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:31][S:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[S:19]([NH:11][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][N:3]=[C:2]2[C:42]1[CH:43]=[CH:44][N:39]=[CH:40][CH:41]=1)(=[O:21])=[O:20])(=[O:29])=[O:30]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 22567083tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate

Product 1

HCID 225672532-methylsulfonyl-N-(3-pyridin-4-yl-1H-indazol-5-yl)benzenesulfonamideYield 15.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Methylsulfonyl-N-(3-pyridin-4-yl-1H-indazol-5-yl)benzenesulfonamide 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, of 380 mg 4-pyridylboronic acid, 40 ml of dimethylformamide, 3.2 ml of a saturated aqueous sodium hydrogencarbonate solution and 42.7 mg of tetrakis(triphenylphosphine)palladium[0]. 100 mg of 2-methylsulfonyl-N-(3-pyridin-4-yl-1H-indazol-5-yl)benzenesulfonamide are thus obtained in the form of a white solid melting at 265° C. (analysis C19H16N4O4S2 % calculated C, 53.26; H, 3.76; N, 13.08; O, 14.94; S, 14.97. % found C, 52.59; H, 3.30; N, 12.89; S, 15.14).

Sources & evidence

ORD record
ord-bef765b73e6e442ba3191a1e3ce0826a
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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