Sodium Iodide → HCID 22176573, compound

HRID 1797197Notes

Reaction equation

HRID 1797197 reaction equation
[OH:1][C:2]([C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6].[H-].[Na+].[F:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([F:30])[CH:29]=1)[CH2:25]Br.[Na+].[I-]>CN(C=O)C.O>[F:21][C:22]1[CH:23]=[C:24]([CH2:25][O:18][C:15]2[CH:14]=[CH:13][C:12]([C:2]([OH:1])([CH3:11])[CH2:3][NH:4][S:5]([CH:8]([CH3:10])[CH3:9])(=[O:7])=[O:6])=[CH:17][CH:16]=2)[CH:27]=[C:28]([F:30])[CH:29]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 5188963,5-Difluorobenzyl bromideHCID 22176571HCID 22176571, compound

Product 1

HCID 22176573HCID 22176573, compoundYield 140.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Procedure

Into a 100 mL-3 neck flask fitted with a stirrer and thermometer, 200 mg of [2-hydroxy-2-(4-hydroxyphenyl)propyl][(methylethyl)sulfonyl]amine in DMF (5 mL) was added dropwise to 35 mg of NaH in DMF (20 mL) while stirring at room temperature under a nitrogen atmosphere. After stirring at this temperature for 30 minutes, 153 mg of 3,5-difluorobenzyl bromide in DMF (5 mL) was added dropwise followed by the addition of 92 mg of NaI portion wise. The reaction was then heated at 100° C. for 2 hours. The mixture was cooled to room temperature and poured into H2O and the desired product was extracted with ethyl acetate. This organic layer was washed with H2O, dried over K2CO3, and concentrated under reduced vacuum to yield 410 mg of a brown oil. This two spot material was purified via silica gel chromatography employing the Chromatotron and using a 4000 micron rotor while eluting with a solvent of hexane/ethyl acetate 1:1. Collection of the bottom spot provided the intermediate title compound (70 mg, 24%) as an oil. Ion spray M.S. 398.1 (M*−1).

Workup

  1. customInto a 100 mL-3 neck flask fitted with a stirrer
  2. stirringAfter stirring at this temperature for 30 minutes
  3. temperatureThe reaction was then heated at 100° C. for 2 hours
  4. temperatureThe mixture was cooled to room temperature
  5. extractionthe desired product was extracted with ethyl acetate
  6. washThis organic layer was washed with H2O
  7. dry with materialdried over K2CO3
  8. concentrationconcentrated under reduced vacuum

Sources & evidence

ORD record
ord-a2f1ba302f3341e796eca1a82c56fd55
Source dataset
uspto-grants-2006_04
Patent number
US07034045B1

Reaction notes

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