Sodium Carbonate → HCID 18363871, compound

HRID 382027Notes

Reaction equation

HRID 382027 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]([C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1)([OH:26])=[O:25]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOC>[O:11]=[C:5]1[NH:6][C:7]2[C:3](/[C:4]/1=[CH:12]/[C:13]1[NH:14][CH:15]=[CH:16][CH:17]=1)=[C:2]([C:30]1[CH:31]=[CH:32][C:27]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=1)[CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 18363871HCID 18363871, compoundYield 112.2%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of (Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (30 mg, 0.089 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (151 μL, 0.303 mmol), (Ph3P)2PdCl2 (3 mg, 0.004 mmol) (Aldrich), and 4-carboxyphenylboronic acid (18 mg, 0.108 mmol) (Lancaster) in 4.5 mL of a 2:1 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 flash chromatography (Merck Silica gel 60, 230-400 mesh, 40% ethyl acetate-hexanes then 50% ethyl acetate-hexanes with 1% glacial acetic acid elution) to yield pure (Z)-4-[2,3-Dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-benzoic acid (yield: 33 mg, 91%) as an orange solid (mp 315-317° C.).

Workup

  1. distillationdistilled water
  2. temperaturewas heated
  3. temperatureat reflux under a nitrogen atmosphere for 20 h
  4. customdirectly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 40% ethyl acetate-hexanes
  5. wash50% ethyl acetate-hexanes with 1% glacial acetic acid elution)

Sources & evidence

ORD record
ord-98569bfbf36c407ab5f7e82661ca9f09
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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