Potassium Iodide → HCID 135961826, compound

HRID 2234128Notes

Reaction equation

HRID 2234128 reaction equation
[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:25]1[CH:30]=[C:29]([C:31]2[CH:36]=[CH:35][N:34]=[CH:33][CH:32]=2)[N:28]=[N:27][C:26]=1[O:37]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si](Cl)(C)C.[I-].[K+]>C(#N)C>[CH2:1]([C:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:17][N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[CH:14][CH:15]=2)[NH:10][C:9]=1[C:25]1[C:26](=[O:37])[NH:27][N:28]=[C:29]([C:31]2[CH:32]=[CH:33][N:34]=[CH:35][CH:36]=2)[CH:30]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 4875Potassium Iodide2×HCID 6397Chlorotrimethylsilane2×HCID 68638304HCID 68638304, compound

Product 1

HCID 135961826HCID 135961826, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

100 mg crude 3-benzyl-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-6-(4-methyl-pi-perazin-1-ylmethyl)-1H-indole are dissolved in 2.4 mL acetonitrile. 75 □L TMSCl and 99 mg potassium iodide are added. The reaction mixture is heated to reflux for 3 hours. Then again 75 □L TMSCl and 99 mg potassium iodide are added and the reaction mixture is refluxed for additional 2 hours. Purification by HPLC affords 31 mg (32%) 4-[3-benzyl-6-(4-methyl-piperazin-1-ylmethyl)-1H-indol-2-yl]-6-pyridin-4-yl-2H-pyridazin-3-one as its trifluoroacetate salt.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. temperaturethe reaction mixture is refluxed for additional 2 hours
  4. customPurification by HPLC

Sources & evidence

ORD record
ord-58d5b86dcd3441efbf892151d9c51a0b
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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