Potassium bis(trimethylsilyl)amide → HCID 53628678, compound

HRID 2262640Notes

Reaction equation

HRID 2262640 reaction equation
[CH2:1]([N:4]1[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH2:5]1)[CH2:2][CH3:3].C[Si](C)(C)[N-][Si](C)(C)C.[K+].[F:26][C:27]([F:40])([F:39])[S:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](F)(=[O:37])=[O:36])=[CH:31][CH:30]=1>C1COCC1>[CH2:1]([N:4]1[CH2:8][CH2:7][C@@H:6]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:35]([C:32]3[CH:33]=[CH:34][C:29]([S:28][C:27]([F:40])([F:26])[F:39])=[CH:30][CH:31]=3)(=[O:37])=[O:36])=[CH:13][CH:14]=2)[CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 45156698HCID 45156698, compoundHCID 57470085HCID 57470085, compound

Product 1

HCID 53628678HCID 53628678, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

4-((S)-1-Propylpyrrolidin-3-yl)phenylamin (50 mg, 0.24 mmol) was dissolved in THF (5 ml) at −78° C. and potassium hexamethyldisilazide (146 mg, 0.73 mmol) added. The solution was stirred at −78° C. for 1 hour and then 4-(trifluoromethylthio)benzene-1-sulfonyl fluoride (64 mg, 0.24 mmol) was added and the solution was allowed to reach room temperature over night. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and NaOH (2M). The organic extract was separated, dried (MgSO4), filtered and concentrated to give the product (97 mg, yield 89%).

Workup

  1. waitto reach room temperature over night
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between ethyl acetate and NaOH (2M)
  4. extractionThe organic extract
  5. customwas separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-31bc064c9fe3473291adc2d55c87ea33
Source dataset
uspto-grants-2010_12
Patent number
US07851463B2

Reaction notes

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