Potassium Carbonate → HCID 15552085, compound

HRID 382018Notes

Reaction equation

HRID 382018 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.[K+].[K+].[F:24][C:25]([F:36])([F:35])[C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=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>[NH:14]1[CH:15]=[CH:16][CH:17]=[C:13]1/[CH:12]=[C:4]1\[C:5](=[O:11])[NH:6][C:7]2[C:3]\1=[C:2]([C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([C:25]([F:36])([F:35])[F:24])[CH:31]=1)[CH:10]=[CH:9][CH:8]=2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 15548052(Z)-1,3-dihydro-4-iodo-3-[(1H-pyrrol-2-yl)methylene]-indol-2-one2×

Product 1

HCID 15552085HCID 15552085, compoundYield 57.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension 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), K2CO3 (25 mg, 0.180 mmol), (Ph3P)4Pd (5 mg, 0.004 mmol) (Aldrich), and 3-(trifluoromethyl)phenylboronic acid (20 mg, 0.110 mmol) (Aldrich) in 2.5 mL of a 1.5:1 mixture of 1,2-dimethoxyethane:distilled water was heated at reflux under a nitrogen atmosphere for 14 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 then 40% ethyl acetate-hexanes elution) to yield pure (Z)-1,3-dihydro-3-[(1H-pyrrol-2-yl)methylene]-4-(3-trifluoromethylphenyl)-2H-indol-2-one (yield 18 mg, 56%) as a yellow solid (mp 197-198° C.).

Workup

  1. distillationdistilled water
  2. temperaturewas heated
  3. temperatureat reflux under a nitrogen atmosphere for 14 h
  4. customdirectly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 25% ethyl acetate-hexanes
  5. wash40% ethyl acetate-hexanes elution)

Sources & evidence

ORD record
ord-be64524e5afe487bb72f3d736b41519c
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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