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

HRID 1691807Notes

Reaction equation

HRID 1691807 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-efd98f9305ee4f9f8b7f9f88907e53a7
Source dataset
uspto-grants-2012_04
Patent number
US08153809B2

Reaction notes

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