Sodium Iodide → HCID 57658448, compound

HRID 1667363Notes

Reaction equation

HRID 1667363 reaction equation
[NH2:1][C:2]1[N:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([OH:15])=[CH:10][C:9]=2[F:16])[C:6](=[O:17])[CH:5]=[CH:4][C:3]=1[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26].Br[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].NC1N(C2C(F)=CC(OCCCCCI)=CC=2F)C(=O)C=CC=1C(=O)C1C=CC(F)=CC=1F>CC(C)=O>[NH2:1][C:2]1[N:7]([C:8]2[C:9]([F:16])=[CH:10][C:11]([O:15][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][Cl:34])=[CH:12][C:13]=2[F:14])[C:6](=[O:17])[CH:5]=[CH:4][C:3]=1[C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=1[F:26]

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 960701-Bromo-5-chloropentaneHCID 58608543HCID 58608543, compoundHCID 67444810HCID 67444810, compound

Product 1

HCID 57658448HCID 57658448, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 6-amino-5-(2,4-difluorobenzoyl)-1-(2,6-difluoro-4-hydroxyphenyl)-pyridin-2(1H)-one (300 mg, 0.79 mmol) in acetone (6 ml) under an atmosphere of nitrogen was added 1-bromo-5-chloropentane (0.115 ml, 0.87 mmol, 1.1 eq), sodium iodide (238 mg, 1.59 mmol, 2 eq) and potassium carbonate (438 mg, 3.17 mmol, 4 eq). The mixture was heated at 70° C. for 16 hours, before being allowed to cool to room temperature and partitioned between EtOAc (50 ml) and water (50 ml). The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography (30% EtOAc in heptane) afforded a 3:2 mixture of the title compound and 6-amino-1-{4-[(5-iodopentyl)oxy]-2,6-difluorophenyl}-5-(2,4-difluorobenzoyl)pyridin-2(1H)-one (142 mg) which was used without further purification.

Workup

  1. temperatureto cool to room temperature
  2. custompartitioned between EtOAc (50 ml) and water (50 ml)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (30% EtOAc in heptane)
  7. customafforded

Sources & evidence

ORD record
ord-b327cb246d3f4045a608e75bf0fba842
Source dataset
uspto-grants-2011_10
Patent number
US08044211B2

Reaction notes

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