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

HRID 366717Notes

Reaction equation

HRID 366717 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.[C:13]([C:16]1[CH:17]=[C:18]([CH:21]=O)[NH:19][CH:20]=1)(=[O:15])[CH3:14].C1COCC1>N1CCCCC1.CC(O)C>[C:13]([C:16]1[CH:17]=[C:18](/[CH:21]=[C:5]2\[C:6](=[O:11])[NH:7][C:8]3[C:4]\2=[C:3]([I:12])[C:2]([F:1])=[CH:10][CH:9]=3)[NH:19][CH:20]=1)(=[O:15])[CH3:14]

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 97956015-Fluoro-4-iodoindolin-2-oneHCID 124151104-Acetyl-1H-pyrrole-2-carboxaldehyde

Product 1

HCID 18366029(Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-iodo-2H-indol-2-one

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8082PiperidineSolvent

Procedure

1,3-Dihydro-5-fluoro-4-iodo-2H-indol-2-one (0.77 g, 2.8 mmol) (see Example 2A, supra) and 4-acetyl-2-formylpyrrole (0.42 g, 3.06 mmol) (Example 90A above) were suspended in 1% piperidine in 2-propanol (12 mL) and THF (5 mL) and heated at 85° C. for 2 h. Yellow precipitate was formed. After cooling to room temperature, product was collected by filtration and washed with aqueous 2-propanol and dried in vacuum oven to yield (Z)-3-[(4-Acetyl-1H-pyrrol-2-yl)methylene]-1,3-dihydro-5-fluoro-4-iodo-2H-indol-2-one. (Yield 0.89 g, 80.8%).

Workup

  1. customYellow precipitate was formed
  2. filtrationproduct was collected by filtration
  3. washwashed with aqueous 2-propanol
  4. customdried in vacuum oven

Sources & evidence

ORD record
ord-8347d42534b7420ebcb35dbc39a80a94
Source dataset
uspto-grants-2000_10
Patent number
US06130239

Reaction notes

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