Pyridine → 5-bromo-6-isocyanato-3-methyl-1-(toluene-4-sulfonyl)-1H-indazole

HRID 1691807Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1691807
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[NH2:11])[N:7]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[N:6]=[C:5]2[CH3:22].N1C=CC=CC=1.[C:29](Cl)(Cl)=[O:30]>C1(C)C=CC=CC=1.CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[N:11]=[C:29]=[O:30])[N:7]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[N:6]=[C:5]2[CH3:22]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 6371PhosgeneHCID 593778015-bromo-3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamine

Produkt 1

HCID 593777255-bromo-6-isocyanato-3-methyl-1-(toluene-4-sulfonyl)-1H-indazole

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

5-Bromo-3-methyl-1-(toluene-4-sulfonyl)-1H-indazol-6-ylamine (138 mg, 0.36 mmol) was dissolved in 5 ml of toluene at room temperature. DMAP (1 eq, 44 mg), pyridine (1.3 eq, 0.04 ml) were added followed by phosgene (1.33 eq, 0.24 ml of a 20% solution in toluene). The mixture was allowed to stir at room temperature for 2 hours, forming a fine white precipitate. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was diluted with dichloromethane and concentrated in vacuo again to give 5-bromo-6-isocyanato-3-methyl-1-(toluene-4-sulfonyl)-1H-indazole (150 mg, quantitative) as a white crystalline solid.

Aufarbeitung

  1. customforming a fine white precipitate
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with dichloromethane
  5. concentrationconcentrated in vacuo again

Quellen und Nachweise

ORD-Eintrag
ord-efd98f9305ee4f9f8b7f9f88907e53a7
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153809B2

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