Sodium Bicarbonate → 2-methylsulfonyl-N-[3-(5-methoxy-1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamide

HRID 25416

Reaction equation

HRID 25416 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.C(OC([N:46]1[C:54]2[C:49](=[CH:50][C:51]([O:55][CH3:56])=[CH:52][CH:53]=2)[CH:48]=[C:47]1B(O)O)=O)(C)(C)C.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:47]1[NH:46][C:54]2[C:49]([CH:48]=1)=[CH:50][C:51]([O:55][CH3:56])=[CH:52][CH:53]=2)(=[O:21])=[O:20])(=[O:29])=[O:30]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 27947161-Boc-5-methoxyindole-2-boronic acidHCID 22567083tert-butyl 3-iodo-5-(N-tert-butoxycarbonyl-2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate

Product 1

HCID 1356219392-methylsulfonyl-N-[3-(5-methoxy-1H-indol-2-yl)-1H-indazol-5-yl]benzenesulfonamideYield 19.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Sources & evidence

ORD record
ord-3e2a4ae2108843d5942a4a178989a99b
Source dataset
uspto-grants-2005_02
Patent number
US06858638B2

Linked notes

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