Stannous Chloride → HCID 22556939, compound

HRID 983807Notes

Reaction equation

HRID 983807 reaction equation
[Br:1][C:2]1[C:3]([OH:31])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-])=O)=[CH:21][CH:20]=2)=[CH:15][C:14]([C:28]([NH2:30])=[NH:29])=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.Cl[Sn]Cl>Cl>[NH2:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:28]([NH2:30])=[NH:29])[CH:15]=3)[NH:10][C:9]=2[C:4]2[CH:5]=[C:6]([CH3:8])[CH:7]=[C:2]([Br:1])[C:3]=2[OH:31])=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 24479Stannous ChlorideHCID 22556990HCID 22556990, compound

Product 1

HCID 22556939HCID 22556939, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Procedure

A mixture of 2-(3-bromo-2-hydroxy-5-methyl-phenyl)-3-(4-nitro-benzyl)-1H-indole-5-carboxamidine 203 (100 mgs, 0.2 mmol), SnCl2 (100 mgs) and 6N HCl is heated at reflux for 1 hr. The reaction is cooled, let stand for 12-18 h, and the residue is isolated. The residue is taken up in 0.1N HCl and purified by reverse phase HPLC (0.01%HCl/acetonitrile) with a 2-90% gradient to yield 42% of 3-(4-amino-benzyl)-2-(3-bromo-2-hydroxy-5-methyl-phenyl)-1H-indole-5-carboxamidine as a white solid (38 mgs, 0.08 mmol).

Workup

  1. temperatureis heated
  2. temperatureat reflux for 1 hr
  3. temperatureThe reaction is cooled
  4. customthe residue is isolated
  5. custompurified by reverse phase HPLC (0.01%HCl/acetonitrile) with a 2-90% gradient

Sources & evidence

ORD record
ord-452327feb55049888294c76a6dcc4063
Source dataset
uspto-grants-2005_03
Patent number
US06867200B1

Reaction notes

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