Potassium Iodide → HCID 44215331, compound

HRID 852096Notes

Reaction equation

HRID 852096 reaction equation
Br[CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=3[O:14][N:13]=2)=[CH:8][CH:7]=1.[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(OCC)(=O)C.C(#N)C>[CH2:22]([NH:29][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=3[O:14][N:13]=2)=[CH:8][CH:7]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 17906346HCID 17906346, compound

Product 1

HCID 44215331HCID 44215331, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Mix 3-[4-(3-bromo-propoxy)-phenyl]-6-fluoro-benzo[d]isoxazole (150 mg, 0.43 mmol), benzylamine (92.2 mg, 0.861 mmol), potassium carbonate(130.6 mg, 0.95 mmol, 2.2 equivalents), potassium iodide (7.2 mg, 0.043 mmol) and 4%-5% aqueous acetonitrile (4-6 mL). Under a nitrogen atmosphere, heat (70°-75° C.) overnight. Dilute reaction mixture with ethyl acetate, filter to remove the solids and concentrate (in vacuo). Purify the crude reaction mixture by column (silica) chromatography using a Waters Sep-Pak 10 g cartridge eluted with ethyl acetate to give the title compound as a solid (89.23 mg, 55.1% Yield). Purity by LC/MS=95%, [M+H]+=377.

Workup

  1. temperatureUnder a nitrogen atmosphere, heat (70°-75° C.) overnight
  2. additionDilute
  3. filtrationfilter
  4. customto remove the solids
  5. concentrationconcentrate (in vacuo)
  6. customPurify the crude
  7. customreaction mixture by column (silica) chromatography
  8. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-3c8b6736da1d4196b35442808488fd50
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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