Sodium Thiosulfate → HCID 22180717, compound

HRID 1795876Notes

Reaction equation

HRID 1795876 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22]C)[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([NH2:16])=[C:10]2[C:17]#[N:18].C[Si](I)(C)C.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[CH3:25][O:24][C:20]1[CH:19]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:21]=1[OH:22])[O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([NH2:16])=[C:10]2[C:17]#[N:18]

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 85247Trimethylsilyl iodideHCID 9881028HCID 9881028, compound

Product 1

HCID 22180717HCID 22180717, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(3,4,5-trimethoxyphenoxy)-2-amino-1H-indole-3-carbonitrile (Example 11) (50 mg; 0.147 mmol) in CH2Cl2 (1.0 ml) was treated with trimethyl silyl iodide (30 ul; 0.2 mmol) and the mixture was stirred at room temperature overnight. The mixture was treated with aqueous Na2S2O3 (0.5 M), the CH2Cl2 evaporated and the mixture extracted with EtOAc. The organic phase was washed with water, brine and dried over MgSO4. Evaporation gave 5-(3,5-dimethoxy-4-hydroxy-phenoxy)-2-amino-1H-indole-3-carbonitrile (50 mg).

Workup

  1. customthe CH2Cl2 evaporated
  2. extractionthe mixture extracted with EtOAc
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customEvaporation

Sources & evidence

ORD record
ord-3fa2754cc7b84f0eb84e49a50289bfc1
Source dataset
uspto-grants-2006_04
Patent number
US07030123B2

Reaction notes

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