Sodium Carbonate → HCID 15552083, compound

HRID 382016Notes

Reaction equation

HRID 382016 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+].[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=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>[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([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:28][CH:27]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 201262(4-Methoxyphenyl)boronic acidHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 15552083HCID 15552083, compoundYield 94.7%

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 (100 mg, 0.298 mmol) (Starting Material 1), 2M aqueous Na2CO3 solution (342 μL, 0.684 mmol), (Ph3P)4Pd (17 mg, 0.015 mmol) (Aldrich), and 4-methoxyphenylboronic acid (52 mg, 0.342 mmol) (Aldrich) in 3 mL of a 2:1 mixture of 1,2-dimethoxyethane:distilled water was heated at 100° C. under a nitrogen atmosphere for 20 h. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with distilled water. The organic layer was concentrated in vacuo to provide a crude yellow-brown solid. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 25% ethyl acetate-hexanes elution) yielded pure (Z)-1,3-dihydro-4-(4-methoxyphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (89.3 mg, 82%) as a yellow solid (mp 222-223° C.).

Workup

  1. distillationdistilled water
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washthe organic layer was washed with distilled water
  4. concentrationThe organic layer was concentrated in vacuo
  5. customto provide a crude yellow-brown solid
  6. washFlash chromatography (Merck Silica gel 60, 230-400 mesh, 25% ethyl acetate-hexanes elution)

Sources & evidence

ORD record
ord-43433ffa541a471193add3f65f8d7feb
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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