Potassium Carbonate → O-Glycidyl-1-fluoro-4-hydroxycarbazole

HRID 1824321Notes

Reaction equation

HRID 1824321 reaction equation
[F:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[C:5]([OH:15])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]1[O:24][C@H:23]1[CH2:25]OS(C1C=C([N+]([O-])=O)C=CC=1)(=O)=O>CC(C)=O>[CH2:25]([O:15][C:5]1[C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:13][C:14]=2[C:2]([F:1])=[CH:3][CH:4]=1)[CH:23]1[O:24][CH2:22]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 146513Benzenesulfonic acid, 3-nitro-, (2R)-2-oxiranylmethyl esterHCID 221478201-Fluoro-4-hydroxycarbazole

Product 1

HCID 22147763O-Glycidyl-1-fluoro-4-hydroxycarbazoleYield 48%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1-fluoro-4-hydroxycarbazole (470 mg, 2 mmol), potassium carbonate (345 mg, 2.5 mmol), (2R)-(−)-glycidyl 3-nitrobenzenesulfonate, (518 mg, 2 mmol), and 20 mL of acetone was heated to reflux for about 18 hours. The reaction was cooled and concentrated in vacuo. The residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was purified via flash silica gel chromatography eluting with 10% ethyl acetate/hexanes to give 247 mg of the title compound.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for about 18 hours
  3. temperatureThe reaction was cooled
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate and water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified via flash silica gel chromatography
  10. washeluting with 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-a7207deb5c164d21a542202e1057649e
Source dataset
uspto-grants-2006_05
Patent number
US07041684B2

Reaction notes

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