Sodium bis(trimethylsilyl)amide → HCID 18951069, compound

HRID 1492443Notes

Reaction equation

HRID 1492443 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1/[CH:15]=[CH:16]/[C:17](=[O:25])[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[C:12]([Cl:26])[CH:11]=[C:10]([Cl:27])[CH:9]=2)=[O:5])[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:38][Si:39]([CH2:42][CH2:43][O:44][CH2:45]Cl)([CH3:41])[CH3:40]>CN(C=O)C.O>[C:19]1([NH:18][C:17](/[CH:16]=[CH:15]/[C:14]2[C:13]3[C:8](=[CH:9][C:10]([Cl:27])=[CH:11][C:12]=3[Cl:26])[N:7]([CH2:45][O:44][CH2:43][CH2:42][Si:39]([CH3:41])([CH3:40])[CH3:38])[C:6]=2[C:4]([O:3][CH2:1][CH3:2])=[O:5])=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 10834984HCID 10834984, compound

Product 1

HCID 18951069HCID 18951069, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a cooled (0°) solution of (E)-Ethyl-3-[2-(phenylcarbamoyl)ethenyl]-4,6-dichloroindole-2-carboxylate (300 mg) in dry DMF (25 ml) a solution of sodium bis-(trimethylsilyl)amide (1M;0.0814 ml) was added dropwise. The resulting mixture was stirred at room temperature for 30 minutes then cooled to 0°. Trimethylsilylethoxymethylchloride (185 mg) was added, and the reaction was stirred for one hour at room temperature. The resulting solution was poured in H2O (20 ml) and extracted with diethylether (15 ml×3). The organic layers were dried, concentrated under vacuum and the product isolated by chromatography on silica gel(CH/EA:83/15) to give the title compound (311 mg). Rf =0.35 CH/EA:85/15

Workup

  1. additionwas added dropwise
  2. temperaturethen cooled to 0°
  3. stirringthe reaction was stirred for one hour at room temperature
  4. extractionextracted with diethylether (15 ml×3)
  5. customThe organic layers were dried
  6. concentrationconcentrated under vacuum
  7. customthe product isolated by chromatography on silica gel(CH/EA:83/15)

Sources & evidence

ORD record
ord-e74a931767a64d3e9c32e7a61ee6aa0e
Source dataset
uspto-grants-1994_12
Patent number
US05374648

Reaction notes

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