Sodium Iodide → HCID 57664590, compound

HRID 1467889Notes

Reaction equation

HRID 1467889 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[O:9][CH2:10][CH2:11]Cl)=[CH:4][CH:3]=1.[I-].[Na+].C(=O)([O-])[O-].[K+].[K+].[CH:28]1([N:31]([CH:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)[S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:43])[F:42])[CH:36]=2)(=[O:34])=[O:33])[CH2:30][CH2:29]1>CCOC(C)=O.O.CCC(C)=O>[CH:28]1([N:31]([CH:45]2[CH2:50][CH2:49][N:48]([CH2:11][CH2:10][O:9][CH:8]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH2:47][CH2:46]2)[S:32]([C:35]2[CH:40]=[CH:39][CH:38]=[C:37]([C:41]([F:44])([F:42])[F:43])[CH:36]=2)(=[O:33])=[O:34])[CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 2773944N-Cyclopropyl-N-piperidin-4-yl-3-(trifluoromethyl)benzenesulfonamideHCID 107793021-[Bis(4-fluorophenyl)methoxy]-2-chloroethane

Product 1

HCID 57664590HCID 57664590, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-[bis(4-fluorophenyl)methoxy]-2-chloroethane (3.0 g, 10.7 mmol), sodium iodide (4.3 g, 28.9 mmol), and MEK (20 mL) was heated at 80° C. for 24 hours. After allowing the reaction to return to ambient temperature it was filtered. To an aliquat of the filtrate (0.78 mmol) was added potassium carbonate (294 mg, 2.13 mmol) and N-cyclopropyl-N-(piperidin-4-yl)-3-trifluoromethylbenzenesulfonamide (0.71 mmol). The mixture was heated at 80° C. for 16 hours. After TLC indicated the reaction to be complete, water and EtOAc were added to the reaction mixture. The phases were separated, and the aqueous phase was extracted twice with EtOAc. The combined organic extracts were washed with water, washed with brine, dried with sodium sulfate, and concentrated. Purification was then carried out using silica gel chromatography as described in Example 22.

Workup

  1. customthe reaction
  2. customto return to ambient temperature
  3. filtrationwas filtered
  4. temperatureThe mixture was heated at 80° C. for 16 hours
  5. customthe reaction
  6. customThe phases were separated
  7. extractionthe aqueous phase was extracted twice with EtOAc
  8. washThe combined organic extracts were washed with water
  9. washwashed with brine
  10. dry with materialdried with sodium sulfate
  11. concentrationconcentrated
  12. customPurification

Sources & evidence

ORD record
ord-4d566a44f1af402a95acb7c78883b500
Source dataset
uspto-grants-2015_04
Patent number
US09000174B2

Reaction notes

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