Sodium Carbonate → HCID 9905796, compound

HRID 382024Notes

Reaction equation

HRID 382024 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+].[C:24]1(B(O)O)[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][CH:25]=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>[C:32]1([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)[C:33]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2545321-Naphthaleneboronic acidHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 9905796HCID 9905796, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

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 (3 mg, 0.003 mmol) (Aldrich), and 1-naphthaleneboronic acid (22.5 mg, 0.131 mmol) (Lancaster) in 3 mL of a 3:1 mixture of 1,2-dimethoxyethane:distilled water was heated at 100° C. under a nitrogen atmosphere for 20 h. The reaction mixture was allowed to cool to room temperature and then directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 20% ethyl acetate-hexanes then 30% ethyl acetate-hexanes elution) to yield a crude solid. Recrystallization from chloroform-pentane provided pure (Z)-1,3-dihydro-4-(1-naphthalenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield 31 mg, 78%) as yellow crystals (mp 210-212° C.).

Workup

  1. distillationdistilled water
  2. temperatureto cool to room temperature
  3. customdirectly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 20% ethyl acetate-hexanes
  4. wash30% ethyl acetate-hexanes elution)
  5. customto yield a crude solid
  6. customRecrystallization from chloroform-pentane provided pure (Z)-1,3-dihydro-4-(1-naphthalenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield 31 mg, 78%) as yellow crystals (mp 210-212° C.)

Sources & evidence

ORD record
ord-a308e17900ec4c969117871c9600f4a0
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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