Trimethylsilyl iodide → HCID 59463816, compound

HRID 1713401Notes

Reaction equation

HRID 1713401 reaction equation
C[O:2][C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([NH:13][C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][N:4]=1.C[Si](I)(C)C>C(Cl)(Cl)Cl>[O:2]=[C:3]1[C:12]2[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=2[C:6]([NH:13][C:14]2[CH:15]=[C:16]([CH:22]=[CH:23][CH:24]=2)[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:5][NH:4]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 59463818HCID 59463818, compound2×

Product 1

HCID 59463816HCID 59463816, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

560 mg (1.7 mmol) of ethyl 3-(1-methoxy-5,6,7,8-tetrahydroisoquinolin-4-ylamino)benzoate (compound 12) are dissolved in 30 ml of chloroform and, at room temperature, 413 mg (2.1 mmol) of trimethylsilyl iodide are added. The mixture is then heated to reflux until complete conversion is reached by means of LCMS. Further trimethylsilyl iodide is added if necessary. For workup, the mixture is washed twice with H2O, dried with Na2SO4 and concentrated. Chromatography on silica gel (CH2Cl2/MeOH 95:5) affords 216 mg of the title compound. Yield: 40%.

Workup

  1. temperatureThe mixture is then heated
  2. temperatureto reflux until complete conversion
  3. washFor workup, the mixture is washed twice with H2O
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d6c1ceb93baf4ecc89d6db11ec1d6e6e
Source dataset
uspto-grants-2010_09
Patent number
US07795278B2

Reaction notes

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