Trimethylsilyl iodide → HCID 22477326, compound

HRID 549085Notes

Reaction equation

HRID 549085 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:19]3[N:27]([S:28]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)(=[O:30])=[O:29])[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[CH:20]=3)=[CH:14][N:15]2[CH3:18])=[CH:11][C:10]=1[O:38][CH3:39])C1C=CC=CC=1.I[Si](C)(C)C>C(#N)C>[OH:8][C:9]1[CH:17]=[C:16]2[C:12]([C:13]([C:19]3[N:27]([S:28]([C:31]4[CH:36]=[CH:35][C:34]([CH3:37])=[CH:33][CH:32]=4)(=[O:30])=[O:29])[C:22]4=[N:23][CH:24]=[CH:25][CH:26]=[C:21]4[CH:20]=3)=[CH:14][N:15]2[CH3:18])=[CH:11][C:10]=1[O:38][CH3:39]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 22477636HCID 22477636, compound

Product 1

HCID 22477326HCID 22477326, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-(6-benzyloxy-5-methoxy-1-methyl-1H-indol-3-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [1.24 g, Reference Example 13(p)] in acetonitrile (100 mL) was treated with iodotrimethylsilane (820 μl). The reaction mixture was stirred at 50° C. for 2 hours and then concentrated in vacuo. The residue was treated with water (40 mL) and the mixture was extracted three times with dichloromethane (100 mL). The combined organic phases were washed with brine (40 mL), then dried over magnesium sulfate and then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (1:1, v/v) to give the title compound (686 mg) as a white foam. TLC: RF=0.27 (cyclohexane/ethyl acetate: 1/1). MS: EI (70 eV); m/z=447 M+. (45%); 292 (100%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with water (40 mL)
  3. extractionthe mixture was extracted three times with dichloromethane (100 mL)
  4. washThe combined organic phases were washed with brine (40 mL)
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of cyclohexane and ethyl acetate (1:1

Sources & evidence

ORD record
ord-cb6eb10b63cf4e20adbcb55365c13434
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

Loading…