1,2-Dimethoxyethane → HCID 59971439, compound

HRID 382019Notes

Reaction equation

HRID 382019 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][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.COCCOC>C(Cl)(Cl)Cl.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>[CH3:24][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

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 59971439HCID 59971439, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

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 (89 μL, 0.178 mmol), (Ph3P)4Pd (5 mg, 0.004 mmol) (Aldrich), and 4-methylphenylboronic acid (15 mg, 0.110 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 18 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, 25% ethyl acetate-hexanes elution) to provide a crude yellow solid containing product. The solid was dissolved in chloroform and precipitation by the addition of hexanes provided pure (Z)-1,3-dihydro-4-(4-methylphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield 19 mg, 71%) as a yellow solid (mp 217-218° C.).

Workup

  1. distillationdistilled water
  2. temperatureto cool to room temperature
  3. customdirectly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 25% ethyl acetate-hexanes elution)
  4. customto provide a crude yellow solid
  5. additioncontaining product
  6. customprecipitation
  7. additionby the addition of hexanes provided pure (Z)-1,3-dihydro-4-(4-methylphenyl)-3-[(1H-pyrrol-2-yl)methylene]-2H-indol-2-one (yield 19 mg, 71%) as a yellow solid (mp 217-218° C.)

Sources & evidence

ORD record
ord-e615014ec22e43d9853e7fe945c1356c
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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