4-Bromobenzene-1,2-diamine → 5-bromo-2-(1H-indazol-3-yl)-3H-benzimidazole

HRID 2182340Notes

Reaction equation

HRID 2182340 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=O)=[N:2]1.[Br:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[C:15]([NH2:20])[CH:14]=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>CN(C)C=O>[Br:12][C:13]1[CH:18]=[CH:17][C:16]2[N:19]=[C:10]([C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][N:2]=3)[NH:20][C:15]=2[CH:14]=1

Participants

5

Reactant 3

HCID 3235934-Bromobenzene-1,2-diamineHCID 656671Sodium PyrosulfiteHCID 178520025HCID 178520025, compound

Product 1

HCID 1354844135-bromo-2-(1H-indazol-3-yl)-3H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Starting with 643 mg of 1H-indazole-3-carboxaldehyde, 816 mg of 4-bromo-1,2-phenylenediamine, and 836.5 mg of sodium metabisulphite in 15 ml of dimethylformamide, and after purification by SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol) followed by a chromatography under pressure on silica, 939 mg of 5-bromo-2-(1H-indazol-3-yl)-3H-benzimidazole are obtained in the form of a brick-red powder.

Workup

  1. customafter purification
  2. washby SPE (SCX phase, washing with methanol, extraction with 2N ammoniacal methanol)
  3. customare obtained in the form of a brick-red powder

Sources & evidence

ORD record
ord-091d04c57bbf4fc782e98eef6a432610
Source dataset
uspto-grants-2005_05
Patent number
US06897208B2

Reaction notes

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