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

HRID 2227771Notes

Reaction equation

HRID 2227771 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-2bbdb7173d6c4526bc6f8de9d7c9d2cc
Source dataset
uspto-grants-2002_07
Patent number
US06413991B1

Reaction notes

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