Sodium Iodide → HCID 24899465, compound

HRID 602723Notes

Reaction equation

HRID 602723 reaction equation
Br[CH2:2][CH2:3][C:4]1[CH:8]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)[N:6]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:5]=1[CH3:26].[I-].[Na+].[C:29]1(=[O:39])[NH:33][C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12.[K]>CN(C=O)C>[C:29]1(=[O:39])[N:33]([CH2:2][CH2:3][C:4]2[CH:8]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=3)[N:6]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:5]=2[CH3:26])[C:32](=[O:34])[C:31]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:30]12

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 24194345Phthalimide potassium saltHCID 24899466HCID 24899466, compound

Product 1

HCID 24899465HCID 24899465, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(2-bromoethyl)-1-(4-fluorophenyl)-2-methyl-5-[4-(methylsulphonyl)phenyl]-1H-pyrrole (0.80 mmol) in dry DMF (10 mL) was added sodium iodide (0.80 mmol) and the resulting mixture was stirred at r.t. for 30 min. Potassium phthalimide (0.90 mmol) was then added, and the reaction mixture was heated at 70° C. for 14 h. After cooling the mixture was poured onto crushed ice and extracted with CH2Cl2. The organic phase was thoroughly washed with water to remove the DMF excess, dried and concentrated under reduced pressure. The residue, purified by flash-chromatography (EtOAc/hexane 1:1 v/v), gave the expected compound as an oil which crystallizes on standing. Yellowish needles from EtOAc Mp 198-201° C. (yield 70%) 1H-NMR (CDCl3) δ ppm: 2.04 (s, 3H), 2.86 (t, 2H, J=7.5), 2.98 (s, 3H), 3.88 (t, 2H, J=7.6), 6.42 (s, 1H), 7.07 (m, 6H), 7.61-7.74 (m, 4H), 7.81-7.85 (m, 2H).

Workup

  1. temperaturethe reaction mixture was heated at 70° C. for 14 h
  2. temperatureAfter cooling the mixture
  3. additionwas poured
  4. customonto crushed ice
  5. extractionextracted with CH2Cl2
  6. washThe organic phase was thoroughly washed with water
  7. customto remove the DMF excess
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue, purified by flash-chromatography (EtOAc/hexane 1:1 v/v)

Sources & evidence

ORD record
ord-1cf92ea65c904399b7e605e11b164d80
Source dataset
uspto-grants-2011_03
Patent number
US07906551B2

Reaction notes

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