Potassium Iodide → HCID 86612053, compound

HRID 1786705Notes

Reaction equation

HRID 1786705 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH:17]=[CH:18][O:19]C)[CH:15]=2)[CH:10]=[C:9]1[C:21]1[CH:26]=[C:25]([C:27]2[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=2)[N:24]=[N:23][C:22]=1[O:33][CH3:34])=[O:7])([CH3:4])([CH3:3])[CH3:2].[I-].[K+].Cl[Si](C)(C)C>C(#N)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][CH:18]=[O:19])[CH:15]=2)[CH:10]=[C:9]1[C:21]1[CH:26]=[C:25]([C:27]2[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=2)[N:24]=[N:23][C:22]=1[O:33][CH3:34])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 67148474HCID 67148474, compound

Product 1

HCID 86612053HCID 86612053, compoundYield 114.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

180 mg 6-(2-methoxyvinyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester are dissolved in 10 mL acetonitrile. Then 196 mg potassium iodide and 125 μL chlorotrimethylsilane are added. The reaction mixture is stirred for 2 hours at rt. The solvent is removed in vacuo and the obtained solid is dissolved in dichloromethane/water. The aqueous phase is extracted five times with dichloromethane, the combined org. phases are dried (MgSO4) and the solvent removed in vacuo. 200 mg crude product are obtained as a mixture of 6-(2-Oxoethyl)-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester and 6-(2-oxoethyl)-2-(3-oxo-6-pyridin-4-yl-2,3-dihydro-pyridazin-4-yl)indole-1-carboxylic acid tert-butyl ester. The mixture is directly used in the next step.

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe obtained solid is dissolved in dichloromethane/water
  3. extractionThe aqueous phase is extracted five times with dichloromethane
  4. dry with materialphases are dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-88b4576dce994509ad8426d3567f2f13
Source dataset
uspto-grants-2009_03
Patent number
US07507734B2

Reaction notes

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