Potassium Iodide → HCID 135961887, compound

HRID 2234137Notes

Reaction equation

HRID 2234137 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([C:23]2[CH:28]=[C:27]([CH2:29][NH:30][CH3:31])[CH:26]=[C:25]([CH2:32][OH:33])[CH:24]=2)[N:20]=[N:19][C:18]=1[O:34]C)=O)(C)(C)C.[I-].[K+].Cl[Si](C)(C)C>C(#N)C>[OH:33][CH2:32][C:25]1[CH:24]=[C:23]([C:21]2[CH:22]=[C:17]([C:9]3[NH:8][C:16]4[C:11]([CH:10]=3)=[CH:12][CH:13]=[CH:14][CH:15]=4)[C:18](=[O:34])[NH:19][N:20]=2)[CH:28]=[C:27]([CH2:29][NH:30][CH3:31])[CH:26]=1

Participants

5

Reactant 3

HCID 4875Potassium IodideHCID 6397ChlorotrimethylsilaneHCID 68637619HCID 68637619, compound

Product 1

HCID 135961887HCID 135961887, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

18 mg of 2-[6-(3-hydroxymethyl-5-methylaminomethyl-phenyl)-3-methoxy-pyridazin-4-yl]-indole-1-carboxylic acid tert-butyl ester is dissolved in 3 ml of acetonitrile and 19 mg of potassium iodide and 12 mg of chlorotrimethylsilane are added. The reaction is heated to 85° C. for 5 h. The reaction is quenched by the addition of a drop of water, the solvent is removed under reduced pressure and the product is purified by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid). Yield 3.5 mg. LC-MS (ES+) 361 (M+H)+.

Workup

  1. customThe reaction is quenched by the addition of a drop of water
  2. customthe solvent is removed under reduced pressure
  3. customthe product is purified by preparative RP-HPLC
  4. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% trifluoroacetic acid)

Sources & evidence

ORD record
ord-16bc6e78ff7241d1bf3f44920799e024
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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