2-Mesitylenesulfonyl chloride → 6-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole

HRID 1862091

Reaktionsgleichung

Reaktionsgleichung von HRID 1862091
[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.CC(C)([O-])C.[Na+].[C:17]1([CH3:29])[CH:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:18]=1[S:25](Cl)(=[O:27])=[O:26]>C1COCC1>[I:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[S:25]([C:18]2[C:19]([CH3:24])=[CH:20][C:21]([CH3:23])=[CH:22][C:17]=2[CH3:29])(=[O:27])=[O:26])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 130462-Mesitylenesulfonyl chlorideHCID 129912416-iodo-1H-indazoleHCID 23676156Sodium t-butoxide

Produkt 1

HCID 218773966-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of 6-iodo-1H-indazole (7.35 g, 30.1 mmol, 1 equiv) in THF (100 mL) cooled to 0° C. under argon, was added sodium t-butoxide (2.89 g, 30.1 mmol, 1 equiv). A color change from orange to red was observed. Mesitylenesulfonyl chloride (6.60 g, 30.1 mmol, 1 equiv) was added in one portion and the ice bath was removed allowing the reaction mixture to warm to 23° C. After 40 min the mixture was quenched with saturated ammonium chloride and partitioned between water and ethyl acetate. The aqueous was extracted a total of 3 times with ethyl acetate. The combined organic material was washed with brine, dried over sodium sulfate and concentrated under reduced pressure to give 6-iodo-1-(2,4,6-trimethyl-benzenesulfonyl)-1H-indazole as an orange solid (12.8 g, 100% yield, 2:1 mixture). 1H NMR (CDCl3) 8.51 (s, 1H), 7.95 (s, 0.66H, major isomer), 7.91 (s, 0.33H, minor isomer), 7.47 (d, 0.33H, J=8.4 Hz), 7.29 (d, 0.33H, J=8.4 Hz), 7.26 (d, 0.66H, J=8.9 Hz), 7.18 (d, 0.66H, 8.9 Hz), 6.84 (s, 2H), 2.51 (s, 6H), 2.15 (s, 3H).

Aufarbeitung

  1. customthe ice bath was removed
  2. customAfter 40 min the mixture was quenched with saturated ammonium chloride
  3. custompartitioned between water and ethyl acetate
  4. extractionThe aqueous was extracted a total of 3 times with ethyl acetate
  5. washThe combined organic material was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-27b29a033c084bdba985f9b81795e361
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534524B1

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