Indole → HCID 54074025, compound

HRID 1168623Notes

Reaction equation

HRID 1168623 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)C.[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1.[F-].[K+].C1OCCOCCOCCOCCOCCOC1>CS(C)=O.C(OCC)(=O)C>[CH3:1][O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 798IndoleHCID 2855718-Crown-6HCID 67976Benzoic acid, 4-fluoro-, ethyl esterHCID 522689Potassium Fluoride

Product 1

HCID 54074025HCID 54074025, compoundYield 21.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

Ethyl-4-fluorobenzoate (4 mL, 27.3 mmol) and indole (3.51 g, 30 mmol) were dissolved in 50 mL of dimethylsulfoxide (DMSO). Potassium fluoride (37% on basic alumina, 12.8 g) and 18-crown-6 (720 mg, 2.73 mmol) were added and the mixture was heated to 120° C. for 24 hours. The reaction was diluted with ethyl acetate and washed with hydrochloric acid (1.0 M, aq.), sodium bicarbonate (sat'd., aq.) and sodium chloride (sat'd., aq.). The organic layer was dried over magnesium sulfate, filtered and the solvent removed. Purification by flash chromatography on silica gel eluted with 5% ethyl acetate, hexane provided 1.45 g (20%) of a white solid

Workup

  1. washwashed with hydrochloric acid (1.0 M, aq.), sodium bicarbonate (sat'd., aq.) and sodium chloride (sat'd., aq.)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent removed
  5. customPurification by flash chromatography on silica gel
  6. washeluted with 5% ethyl acetate, hexane

Sources & evidence

ORD record
ord-f22c6c8dadee4679b8e5e6577272c645
Source dataset
uspto-grants-2003_09
Patent number
US06624309B1

Reaction notes

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