N-Iodosuccinimide → HCID 86725336, compound

HRID 925226Notes

Reaction equation

HRID 925226 reaction equation
[Br:1][C:2]1[C:18]([OH:19])=[CH:17][C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1.C1C(=O)N([I:27])C(=O)C1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:18]([OH:19])=[C:17]([I:27])[C:5]2[CH2:6][CH2:7][N:8]([C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:9][CH2:10][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86725335HCID 86725335, compound

Product 1

HCID 86725336HCID 86725336, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Into a 100 ml flask, the product of step (e) (1.03 g, 3.05 mmol) dissolved in TFA (10 ml) was added. To this stirred solution, NIS (828 mg, 3.68 mmol) was added. The reaction mixture was stirred at room temperature for 45 minutes, then carefully poured over ice-cold saturated aqueous NaHCO3 (200 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the crude product. Purification by silica-gel chromatography (gradient elution: 0 to 30% EtOAc in hexanes) gave the sub-title compound as a yellow solid (166 mg). 1H NMR (300 MHz, CDCl3) δ 7.29 (s, 1H); 5.99 (s, 1H); 3.76-3.67 (m, 4H); 3.33-3.30 (m, 2H); 3.00-2.96 (m, 2H); MS: ESI (positive): 464, 466 (M+H).

Workup

  1. additionwas added
  2. extractionThe aqueous mixture was extracted with EtOAc (3×)
  3. washThe combined EtOAc extracts were washed with brine
  4. dry with materialdried over Na2SO4, and solvent
  5. customevaporated in vacuo
  6. customto give the crude product
  7. customPurification
  8. washby silica-gel chromatography (gradient elution: 0 to 30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-0850555b710248aa85f7dcd55d06bcab
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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