Acetone → HCID 59973113, compound

HRID 428646Notes

Reaction equation

HRID 428646 reaction equation
[I-].CC(OC([N:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[CH2:14][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)(C)C.[H-].[Na+].[I:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41](=[O:46])[C:40]2=O.CC(C)=O>CN(C=O)C>[I:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][C:41](=[O:46])/[C:40]/2=[CH:14]\[C:10]1[NH:9][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 24758Sodium hydrideHCID 886955-IodoisatinHCID 23031350HCID 23031350, compound

Product 1

HCID 59973113HCID 59973113, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of [[1-[[(1,1-dimethylethyl)oxy]carbonyl]-1H-pyrrol-2-yl]methyl]triphenylphosphonium iodide (2.3 g, 4.0 mmol) (prepared according to the procedure of: V. H. Rawal et. al., J. Org. Chem. 1987, 52(1), 19-28) in 36 mL DMF at 0° C. under argon, was added slowly NaH (0.13 g, 5.4 mmol). The mixture was stirred at 0° C. for 45 min. The solution was then allowed to warm to room temperature and 5-iodoisatin (1.0 g, 3.66 mmol) was added. The solution was heated at reflux for 15 h, at which time acetone (1 mL) was added and the solvent mixture was evaporated. The residue was then purified via flash column chromatography (25% EtOAc/hex) to yield (Z)-1,3-dihydro-5-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one. (Yield 1.05 g, 83%).

Workup

  1. temperatureto warm to room temperature
  2. temperatureThe solution was heated
  3. additionwas added
  4. customthe solvent mixture was evaporated
  5. customThe residue was then purified via flash column chromatography (25% EtOAc/hex)

Sources & evidence

ORD record
ord-7ae1d9cb6eb74bf08faf84e3034b5464
Source dataset
uspto-grants-2001_11
Patent number
US06313310B1

Reaction notes

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