1-Iodopentane → HCID 19434917, compound

HRID 1736136Notes

Reaction equation

HRID 1736136 reaction equation
[NH2:1][C:2]1[C:7]2[C:8](=[O:26])[CH:9]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([F:25])[CH:13]=3)[O:11][C:6]=2[C:5]([F:27])=[CH:4][C:3]=1[F:28].[H-].[Na+].I[CH2:32][CH2:33][CH2:34][CH2:35][CH3:36].[Cl-].[NH4+]>CN(C)C=O>[F:28][C:3]1[CH:4]=[C:5]([F:27])[C:6]2[O:11][C:10]([C:12]3[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:14]([F:25])[CH:13]=3)=[CH:9][C:8](=[O:26])[C:7]=2[C:2]=1[NH:1][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36]

Participants

6

Reactant 4

HCID 123351-Iodopentane2×HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19434934HCID 19434934, compound

Product 1

HCID 19434917HCID 19434917, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

505 mg (1.29 mmol) of the resulting 5-amino-6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-4H-1-benzopyran-4-one was dissolved in 15 ml of dimethylformamide under argon atmosphere, 155 mg of sodium hydride (60% oil dispersion) and 0.35 ml of 1-iodopentane were added and the mixture was stirred at the same temperature for 30 minutes. 0.17 ml of 1-iodopentane was added and the mixture was stirred for additional 2 hours. An aqueous saturated solution of ammonium chloride was added to the reaction solution and the mixture was extracted twice with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and dried over anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform) to give 333 mg (56%) of 6,8-difluoro-2-(3-fluoro-4-pivaloylaminophenyl)-5-pentylamino-4H-1-benzopyran-4-one.

Workup

  1. stirringthe mixture was stirred for additional 2 hours
  2. extractionthe mixture was extracted twice with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-873912f65530425ba24e131fc7ec475d
Source dataset
uspto-grants-1996_07
Patent number
US05539112

Reaction notes

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