Lithium Carbonate → HCID 22147703, compound

HRID 2119835Notes

Reaction equation

HRID 2119835 reaction equation
[F:1][C:2]1[C:14]2[NH:13][C:12]3[CH2:11][CH2:10][CH2:9][C:8](=[O:15])[C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Li+].[Li+].[Br-].[Li+]>[Cu].C(OCC)(=O)C>[F:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[C:8]([OH:15])[CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11125Lithium CarbonateHCID 82050Lithium BromideHCID 221477458-Fluoro-1,2,3,9-tetrahydro-4H-carbazol-4-one

Product 1

HCID 22147703HCID 22147703, compoundYield 28.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-fluoro-5-oxo-5,6,7,8-tetrahydrocarbazole (111 mg, 0.55 mmol), copper II bromide (244 mg, 1.09 mmol), and 5 mL of ethyl acetate was heated to reflux for about 12 hours. The reaction was cooled to room temperature, treated with celite, and then filtered. The reaction was partitioned between aqueous sodium bicarbonate and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in 5 mL of dimethylformamide and lithium carbonate (52 mg, 0.7 mmol) and lithium bromide (61 mg, 0.7 mmol) were added. The resulting mixture was heated to reflux for 1.5 hours. The reaction was concentrated in vacuo and the crude product was purified via flash silica gel chromatography eluting with 15% ethyl acetate/hexanes to give 32 mg of the title compound. Yield: 18%. 1H NMR. MS(FD).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 12 hours
  3. additiontreated with celite
  4. filtrationfiltered
  5. customThe reaction was partitioned between aqueous sodium bicarbonate and ethyl acetate
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. dissolutionThe residue was dissolved in 5 mL of dimethylformamide
  10. temperatureThe resulting mixture was heated
  11. temperatureto reflux for 1.5 hours
  12. concentrationThe reaction was concentrated in vacuo
  13. customthe crude product was purified via flash silica gel chromatography
  14. washeluting with 15% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-914f220eb29e44dab54a2230ca5be1e9
Source dataset
uspto-grants-2004_02
Patent number
US06686372B2

Reaction notes

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