Water → HCID 10171984, compound

HRID 1246003Notes

Reaction equation

HRID 1246003 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20]C)=[C:14]([O:22][CH3:23])[CH:13]=3)=[CH:8][CH:9]=2)[C:4]([C:24]#[N:25])=[CH:3]1.C[Si](I)(C)C.O>C(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:13]=[C:14]([O:22][CH3:23])[C:15]([OH:20])=[C:16]([O:18][CH3:19])[CH:17]=3)=[CH:8][CH:9]=2)[C:4]([C:24]#[N:25])=[CH:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 85247Trimethylsilyl iodideHCID 21915661HCID 21915661, compound

Product 1

HCID 10171984HCID 10171984, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-methyl-3-cyano-5-(3,4,5-trimethoxyphenoxy)-1H-indole (500 mg; 1.47 mmol) in CH2Cl2 (10 ml) was added trimethylsilyl iodide (831 μl; 5.84 mmol). After stirring at room temperature under argon atmosphere for 2 h30, the mixture was poured into cold water, extracted with ethyl acetate. The organic phase was evaporated and the residue was purified by flash chromatography on silica gel, eluting with CH2Cl2/Et2O 1:1 to give 1-methyl-3-cyano-5-(4-hydroxy-3,5-dimethoxyphenoxy)-1H-indole: (244 mg)

Workup

  1. extractionextracted with ethyl acetate
  2. customThe organic phase was evaporated
  3. customthe residue was purified by flash chromatography on silica gel
  4. washeluting with CH2Cl2/Et2O 1:1

Sources & evidence

ORD record
ord-722ef850fe754ec8a31af1256792770b
Source dataset
uspto-grants-2006_10
Patent number
US07125906B2

Reaction notes

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