Sodium Iodide → 2-[4-[N-acetyl-N-(3-iodopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one

HRID 1736195Notes

Reaction equation

HRID 1736195 reaction equation
[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7]Cl)(=[O:3])[CH3:2].[I-:30].[Na+]>C(C(C)=O)C>[C:1]([N:4]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][C:17]3[C:25]([F:26])=[CH:24][C:23]([F:27])=[C:22]([NH2:28])[C:18]=3[C:19](=[O:21])[CH:20]=2)=[CH:11][C:10]=1[F:29])[CH2:5][CH2:6][CH2:7][I:30])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 19434902HCID 19434902, compound

Product 1

HCID 194348032-[4-[N-acetyl-N-(3-iodopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-oneYield 93.2%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

6.31 g (14.9 mmol) of 2-[4-[N-acetyl-N-(3-chloropropyl) amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one obtained in Example 50 was dissolved in 240 mL of methyl ethyl ketone, 6.09 g (149 mmol) of sodium iodide was added and the mixture was heated at reflux for 4 hours. The reaction solution was cooled to room temperature and filtered. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (chloroform-chloroform:methanol=50:1) to give 7.17 g of 2-[4-[N-acetyl-N-(3-iodopropyl)amino]-3-fluorophenyl]-5-amino-6,8-difluoro-4H-1-benzopyran-4-one (yield: 93%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform-chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-f3451547e7174bd9954b44daf2fac2fa
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

Loading…