Iodine → HCID 86691622, compound

HRID 624311Notes

Reaction equation

HRID 624311 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([CH:17]=O)[C:6]=2[C:19]=1[F:20].[CH2:21]([NH2:24])[CH2:22][NH2:23].C(=O)([O-])[O-].[K+].[K+].II>CC(O)(C)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]3[NH:23][CH2:22][CH2:21][N:24]=3)[C:6]=2[C:19]=1[F:20]

Participants

6

Reactant 4

HCID 807IodineHCID 3301EthylenediamineHCID 11430Potassium CarbonateHCID 71743951HCID 71743951, compound

Product 1

HCID 86691622HCID 86691622, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of 5-chloro-4-fluoro-2-(4-fluorophenyl)benzofuran-3-carbaldehyde (1.2 g, 4.10 mmol) and ethylenediamine (0.277 m, 4.10 mmol) in t-BuOH (15 ml) under a N2 atmosphere in a 50 ml RB flask was stirred at room temperature for 30 minutes. Potassium carbonate (0.567 g, 4.10 mmol) followed by iodine (1.041 g, 4.10 mmol) were then added and the reaction mixture was heated at 70° C. for 2 hours. The solvent was removed and the residue diluted with ethyl acetate. The mixture was washed with 10% sodium thiosulfate solution. The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was purified by using combiflash silica column using 8% methanol in chloroform as an eluent. The desired fractions were collected and concentrated to give the titled product (0.7 g, 52%). 1H NMR (400 MHz, CDCl3): δ 7.77-7.75 (m, 2H), 7.37-7.34 (m, 1H), 7.27-7.16 (m, 3H), 3.90 (s, 4H).

Workup

  1. additionwere then added
  2. temperaturethe reaction mixture was heated at 70° C. for 2 hours
  3. customThe solvent was removed
  4. additionthe residue diluted with ethyl acetate
  5. washThe mixture was washed with 10% sodium thiosulfate solution
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified
  10. customThe desired fractions were collected
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-69e2d26a34c647759db237b795bdc381
Source dataset
uspto-grants-2016_04
Patent number
US09303020B2

Reaction notes

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