Potassium Iodide → HCID 58928278, compound

HRID 852106Notes

Reaction equation

HRID 852106 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:15]3[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=3[O:13][N:12]=2)=[CH:7][CH:6]=1.[CH2:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH2:24][CH2:23][NH:22]1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>C(#N)C>[F:20][C:18]1[CH:17]=[CH:16][C:15]2[C:11]([C:8]3[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][N:22]4[CH2:23][CH2:24][C:25]5[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=5)[CH2:21]4)=[CH:6][CH:7]=3)=[N:12][O:13][C:14]=2[CH:19]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 17906318HCID 17906318, compound

Product 1

HCID 58928278HCID 58928278, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Combine 3-[4-(2-bromo-ethoxy)-phenyl]-6-fluoro-benzo[d]isoxazole (200 mg, 0.595 mmol), 1,2,3,4-tetrahydroisoquinoline (0.08 mL, 0.595 mmol), potassium carbonate (181 mg, 1.31 mmol), potassium iodide (10 mg, 0.06 mmol) and 4% aqueous acetonitrile. Stir at 70° C. for 18 hours and cool to room temperature. Filter the reaction mixture and wash the solids with dichloromethane. Evaporate the filtrate to give the title compound as a brown solid (130 mg, 56% Yield). Purity by LC/MS=68%, [M+H]+=389.

Workup

  1. temperaturecool to room temperature
  2. filtrationFilter the reaction mixture
  3. washwash the solids with dichloromethane
  4. customEvaporate the filtrate

Sources & evidence

ORD record
ord-b92ab4a4ca5d4f2587c4f010e7ae001c
Source dataset
uspto-grants-2007_08
Patent number
US07253165B2

Reaction notes

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