Isatin → 7-Phenylisatin

HRID 2375515Notes

Reaction equation

HRID 2375515 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)(O)[O-].[Na+].IC1C=CC=C2C=1NC(=O)C2=O>O.ClCCl.C(OCC)(=O)C.COCCOC>[C:12]1([C:10]2[CH:9]=[CH:8][CH:7]=[C:6]3[C:11]=2[NH:1][C:2](=[O:3])[C:4]3=[O:5])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

9

Reactant 4

HCID 7054IsatinHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 40437057-Iodoisatin

Product 1

HCID 107754477-Phenylisatin

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared according to the procedure described by Lisowski et al. J. Org. Chem., 2000, 65, 4193. To a 1 L 3-necked round-bottomed flask fitted with a reflux condenser were added intermediate 6 (2.0 g, 7.33 mmol) and tetrakis[triphenylphosphine]palladium (0.424 g, 0.367 mmol), followed by 225 mL 1,2-dimethoxyethane. The atmosphere in the reaction vessel was made inert by opening to vacuum, then to a positive pressure of nitrogen (3×). Phenylboronic acid (Aldrich, 0.983 g, 8.06 mmol) and a solution of sodium bicarbonate (1.23 g, 14.7 mmol) in 225 mL water were added, and the evacuation/nitrogen procedure repeated one more time. The reaction mixture was then refluxed until t.l.c. (10% ethyl acetate in dichloromethane) showed complete disappearance of 7-iodoisatin (1-2 hours). After cooling to room temperature, the 1,2-dimethoxyethane was removed under reduced pressure. The residue was diluted with 1M aqueous hydrochloric acid and extracted into ethyl acetate (3×). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated under reduced pressure to give crude 7-phenylisatin 7.

Workup

  1. customThis compound was prepared
  2. customTo a 1 L 3-necked round-bottomed flask fitted with a reflux condenser
  3. temperatureThe reaction mixture was then refluxed until t.l.c
  4. customthe 1,2-dimethoxyethane was removed under reduced pressure
  5. additionThe residue was diluted with 1M aqueous hydrochloric acid
  6. extractionextracted into ethyl acetate (3×)
  7. washThe organic layer was washed with brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-6f87a9488d614ab484206136d967cb65
Source dataset
uspto-grants-2008_12
Patent number
US07465799B2

Reaction notes

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