Benzo(B)Thiophene-2-Boronic Acid → n-(3-Benzo[b]thiophen-2-yl-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide

HRID 1452890

Reaktionsgleichung

Reaktionsgleichung von HRID 1452890
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=3[S:21]([CH3:24])(=[O:23])=[O:22])(=[O:14])=[O:13])[CH:9]=2)[N:4](C(OC(C)(C)C)=O)[N:3]=1.B(O)(O)[C:33]1[S:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:34]=1.C(=O)([O-])O.[Na+]>CN(C)C=O>[S:41]1[C:33]([C:2]2[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([NH:11][S:12]([C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[S:21]([CH3:24])(=[O:23])=[O:22])(=[O:13])=[O:14])[CH:9]=3)[NH:4][N:3]=2)=[CH:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][C:40]1=2

Komponenten

5

Edukt 3

HCID 2359Benzo(B)Thiophene-2-Boronic AcidHCID 516892Sodium BicarbonateHCID 22567134Tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate

Produkt 1

HCID 22567032n-(3-Benzo[b]thiophen-2-yl-1h-indazol-5-yl)-2-methylsulfonylbenzenesulfonamideAusbeute 35,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-(3-Benzo[b]thiophen-2-yl-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide can be obtained as described in Example 59 from 0.5 g of tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate, 300 mg of thianaphthene-2-boronic acid, 20 ml of dimethylformamide, 1.9 ml of a saturated aqueous solution of sodium hydrogencarbonate and 25 mg of tetrakis(triphenylphosphine)palladium[0]. 150 mg of N-(3-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-2-methylsulfonylbenzenesulfonamide are thus obtained in the form of a white solid melting at 270° C. (analysis C22H17N3O4S3% calculated C, 54.64; H, 3.54; N, 8.69; O, 13.23; S, 19.89. % found C, 54.59H, 3.47; N, 8.79; S, 19.98).

Quellen und Nachweise

ORD-Eintrag
ord-cb6a70082b564274adb437cdf44d43d7
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473701B2

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