Water → N-[3-(3-bromophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide

HRID 1452921Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452921
[Br:1][C:2]1[CH:3]=[C:4](B(O)O)[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])O.[Na+].I[C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([NH:26][S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[S:36]([CH3:39])(=[O:38])=[O:37])(=[O:29])=[O:28])[CH:24]=2)[N:19](C(OC(C)(C)C)=O)[N:18]=1.O>CN(C)C=O>[Br:1][C:2]1[CH:3]=[C:4]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH:26][S:27]([C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[S:36]([CH3:39])(=[O:38])=[O:37])(=[O:28])=[O:29])[CH:24]=3)[NH:19][N:18]=2)[CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 2734318(3-Bromophenyl)boronic acidHCID 22567134Tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate

Produkt 1

HCID 22567155N-[3-(3-bromophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamideAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

N-[3-(3-Bromophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide can be obtained in the follow way: 1.6 g of (3-bromophenyl)boronic acid, 8.7 ml of a saturated aqueous sodium hydrogencarbonate solution and 0.11 g of tetrakis(triphenylphosphine)palladium[0] are added successively to a suspension, maintained under an atmosphere of argon, of 2.3 g of tert-butyl 3-iodo-5-(2-methylsulfonylbenzenesulfonylamino)indazole-1-carboxylate in 90 ml of dimethylformamide. The reaction mixture is refluxed for 5 hours. After cooling to a temperature in the region of 20° C., the reaction mixture is hydrolyzed with 200 ml of water and extracted with 200 ml and then 100 ml of ethyl acetate. The pooled organic extracts are dried over magnesium sulfate, filtered and then concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. The brown oil thus obtained is purified by chromatography on a silica column (particle size 63-200 μm), eluting with a dichloromethane/methanol (99/1 by volume) mixture. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.4 g of N-[3-(3-bromophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide are obtained in the form of a yellow lac. This product is repurified by chromatography on a silica column (particle size 63-200 μm), with pure dichloromethane as eluent. The fractions containing the expected product are pooled and concentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C. 0.73 g of N-[3-(3-bromophenyl)-1H-indazol-5-yl]-2-methylsulfonylbenzenesulfonamide are obtained in the form of a white foam melting at 104° C.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. extractionextracted with 200 ml
  3. dry with materialThe pooled organic extracts are dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C
  6. customThe brown oil thus obtained
  7. customis purified by chromatography on a silica column (particle size 63-200 μm)
  8. washeluting with a dichloromethane/methanol (99/1 by volume) mixture
  9. additionThe fractions containing the expected product
  10. concentrationconcentrated to dryness under reduced pressure (2 kPa) at a temperature in the region of 40° C

Quellen und Nachweise

ORD-Eintrag
ord-62a570a676b04063ad3a54282628be02
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473701B2

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