Sodium Carbonate → HCID 18363919, compound

HRID 382022Notes

Reaction equation

HRID 382022 reaction equation
I[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1/[C:4](=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)/[C:5](=[O:11])[NH:6]2.C([O-])([O-])=O.[Na+].[Na+].[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([C:2]2[CH:10]=[CH:9][CH:8]=[C:7]3[C:3]=2/[C:4](=[CH:12]/[C:13]2[NH:14][CH:15]=[CH:16][CH:17]=2)/[C:5](=[O:11])[NH:6]3)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 18363919HCID 18363919, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (40 mg, 0.119 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (119 μL , 0.238 mmol), (Ph3P)4Pd (5 mg, 0.004 mmol) (Aldrich), and 4-chlorophenylboronic acid (21 mg, 0.134 mmol) (Aldrich) in 4 mL of a 3:1 mixture of 1,2-dimethoxyethane:distilled water was heated at reflux under a nitrogen atmosphere for 20 h. The reaction mixture was allowed to cool to room temperature and then directly purified by column chromatography. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 20% ethyl acetate-hexanes elution) provided a crude yellow solid. Recrystallization from chloroform-pentane yielded pure (Z)-4-(4-chlorophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (34 mg, 89%) as a yellow solid (mp 188-190° C.).

Workup

  1. distillationdistilled water
  2. temperaturewas heated
  3. temperatureat reflux under a nitrogen atmosphere for 20 h
  4. customdirectly purified by column chromatography
  5. washFlash chromatography (Merck Silica gel 60, 230-400 mesh, 20% ethyl acetate-hexanes elution)
  6. customprovided a crude yellow solid
  7. customRecrystallization from chloroform-pentane yielded pure (Z)-4-(4-chlorophenyl)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (34 mg, 89%) as a yellow solid (mp 188-190° C.)

Sources & evidence

ORD record
ord-3ead7bdc9d4345e8a1ce295655dc70e2
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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