Water → (Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

HRID 382012Notes

Reaction equation

HRID 382012 reaction equation
[F:1][C:2]1[C:3]([I:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]2.O>N1CCCCC1.CC(O)C>[F:1][C:2]1[C:3]([I:12])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])/[C:5]/2=[CH:9]\[C:8]1[NH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 962WaterHCID 97956015-Fluoro-4-iodoindolin-2-one2×

Product 1

HCID 18363869(Z)-1,3-dihydro-5-fluoro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8082PiperidineSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 1,3-dihydro-5-fluoro-4-iodo-2H-indol-2-one (1.40 g, 5.05 mmol) (see Starting Material 10), and excess 2-pyrrolecarboxyaldehyde (0.60 g, 6.3 mmol) (Aldrich) in 1% piperidine in 2-propanol (20 mL) was heated at 85° C. for 2.25 h. Hot water (20 mL) was added. On cooling, the crystallized product was filtered off, washed with aqueous 2-propanol and dried. (Yield 1.50 g, 84%).

Workup

  1. temperatureOn cooling
  2. filtrationthe crystallized product was filtered off
  3. washwashed with aqueous 2-propanol
  4. customdried

Sources & evidence

ORD record
ord-cea2ac5f76fa41eaab805b3196bddd1a
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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